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Processes and intermediates for prepn. of 1,3-diazin-b 6-ones and uracils

A kind of technology of oxazine, C1-C6

Inactive Publication Date: 2002-04-10
BASF AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this method is not very satisfactory for the preparation of 2-(N,N-disubstituted)amino-4-(perfluoroalkyl)-1,3-oxazin-6-one compounds, because the The required imidoyl chloride hydrochloride compound is difficult to handle and relatively expensive

Method used

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  • Processes and intermediates for prepn. of 1,3-diazin-b 6-ones and uracils

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Preparation of 3-[(N,N-dimethylcarbamoyl)amino]-4,4,4-[ethyl trifluorocrotonate, (Z)-

[0059]Add ethyl 3-amino-4,4,4-trifluorocrotonate (18.4 g, 100 mmol) to sodium hydride (60% / mineral oil, 9.6 g, 250 mmol) over 60 minutes at 5°C under nitrogen atmosphere in a stirred solution in N,N-dimethylformamide (60 mL). The reaction mixture was warmed to room temperature and held at room temperature for 15 minutes, cooled to 5°C and treated with dimethylcarbamoyl chloride (21.6 g, 200 mmol) over 60 minutes. The resulting solution was then warmed to room temperature for 2 hours, diluted with water (150 mL), and extracted with ethyl acetate (2 x 150 mL). The combined organic layers were dried, filtered and concentrated, and the mineral oil layer was removed to give a residue. The residue was purified by flash column chromatography on silica gel eluting with 85:15 hexane / ethyl acetate solution to afford the title product as a yellow liquid (18.1 g, 71% yield): 1 H NMR (DMSO-d...

Embodiment 2

[0065] Preparation of 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one

[0066] 3-[N-(N,N-Dimethylcarbamoyl)amino]-4,4,4-trifluorocroton was treated with phosphorus pentachloride (4.16 g, 0.02 mol) in 3 batches at 15 min intervals A solution of ethyl acetate (5.08 g, 0.02 mol) in phosphorus oxychloride (3 mL) was stirred for 30 minutes and treated with ice and water. The resulting aqueous mixture was extracted with ethyl acetate. The organic layer was washed sequentially with saturated sodium bicarbonate and water and evaporated to give the title product as a white solid (3.9 g, 93.8% yield), 1 H and 19 F NMR confirmed that it was identical to a sample prepared by a literature method (Bull. Soc. Chem. Belg. 101, 313, 1992). The title product was further purified by recrystallization from heptane (74.5% crystallization yield).

[0067] Using essentially the same method, but replacing 3-[N-(N,N- Dimethylcarbamoyl)amino]-4,4,4-trifluorocrotonate, 2-diethylamino-4-(t...

Embodiment 3

[0069] Preparation of 3-isopropyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

[0070] Isopropylamine (1.2 g, 20.3 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 6 mL) were added to 2-dimethylamino-4-tris Fluoromethyl-6H-1,3-oxazin-6-one (4.0 g, 19.2 mmol) in solution in xylene (34 mL). The resulting reaction mixture was heated at 100 °C for 3 hours, cooled, washed with 5 wt.% HCl (40 mL), and extracted with ethyl acetate. The combined organic phases were concentrated and triturated with heptane. The solid was filtered off and dried to afford the title product as a yellow powder (2.3 g, 54% yield, mp 127-129°C), which 1 H NMR (DMSO-d 6 ) δ 6.11(1H, s), 4.96(1H, sp), 1.35(6H, d); and 19 F NMR δ-68.9(s) confirmed it to be the desired product.

[0071] Using essentially the same procedure, but using the appropriate amine, the following compounds were obtained:

[0072] Q acid / base solvent mp(°C) yield (%)(S)-(+)-CH(CH 3 )C 2 h 5 DBU Toluene 92-95 27(R)-...

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PUM

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Abstract

An improved process and intermediate compounds (N) for the preparation of 2-(N,N-disubstituted)amino-4-(perfluoroalkyl)-1,3-oxazin-6-one compounds having structural formula (I) and an improved process for the preparation of 6-(perfluoroalkyl)uracil compounds having structural formula (V).

Description

Background of the invention [0001] 6-(Perfluoroalkyl)uracil compounds are useful as herbicides and methods for their preparation are known in the art. 6-(perfluoroalkyl)uracil compounds can be prepared by reacting 2-(N,N-disubstituted)amino-4-(perfluoroalkyl)-1,3-oxazin-6-ones with amine compounds be made of. [0002] Bull.Soc.Chem.Belg., 101(4), pp. 313-321 (1992) discloses that by using ethyl 3-amino-4,4,4-trifluorocrotonate and imidoyl chloride hydrochloride ( phosgeneiminium chloride) compound to prepare 2-(N,N-dialkyl)amino-4-(trifluoromethyl)-1,3-oxazin-6-one compound. However, this method is not very satisfactory for the preparation of 2-(N,N-disubstituted)amino-4-(perfluoroalkyl)-1,3-oxazin-6-one compounds, because the The desired imidoyl chloride hydrochloride compound is difficult to handle and relatively expensive. Therefore, there is a need in the art to avoid the use of imidoyl chloride hydrochloride compounds for the preparation of 2-(N,N-disubstituted)amino-...

Claims

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Application Information

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IPC IPC(8): C07B61/00C07C273/18C07C275/20C07D239/54C07D261/20C07D265/06C07D275/04C07D295/215C07D413/04C07D417/04
CPCC07D295/215C07D239/54C07D413/04C07C275/20C07D417/04C07D265/06
Inventor V·卡梅斯瓦兰
Owner BASF AG
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