A kind of synthesis method of iodine catalyzed thiourea desulfurization to prepare substituted guanidine
A technology of iodine-catalyzed thiourea and synthesis method, which is applied in the field of synthesis and achieves the effect of high atom economy
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Embodiment 1
[0021] Preparation of N,N'-di-tert-butoxycarbonyl-N"-(4-methoxy)phenylguanidine
[0022] The structural formula is:
[0023]
[0024] At room temperature, 4-methoxyaniline (24mg, 0.2mmol) was dissolved in 3mL PhMe solution, followed by adding N,N'-Boc thiourea (66 mg, 0.24mmol), I 2 (5mg, 0.02mmol), 70% TBHP (39mg, 0.3mmol). After the addition was complete, the reaction was continued at room temperature until TLC showed complete conversion of starting material. Thereafter, the reaction solution was diluted with ethyl acetate (50 ml) and washed three times with saturated brine (10 mL). The obtained organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained crude product was separated by column chromatography with ethyl acetate / petroleum ether=(1:9) to obtain N,N′-di-tert-butoxycarbonyl-N″- Preparation of phenylguanidine (58 mg, 79% yield). 1 H NMR (500MHz, CDCl 3 )δ11.64(s,1H), 10.18(s,1H),7.49(d,J=9.0Hz,2H),6.85(d,J=9.0...
Embodiment 2
[0026] Preparation of N,N'-di-tert-butoxycarbonyl-N"-(4-methoxy)phenylguanidine
[0027] The structural formula is:
[0028]
[0029] At room temperature, 4-methoxyaniline (24mg, 0.2mmol) was dissolved in 3mL of PhMe solution, followed by adding N,N'-Boc thiourea (66 mg, 0.24mmol), Bu 4 NI (7 mg, 0.02 mmol), 70% TBHP (39 mg, 0.3 mmol). After the addition was complete, the reaction was continued at room temperature until TLC showed complete conversion of starting material. Thereafter, the reaction solution was diluted with ethyl acetate (50 ml) and washed three times with saturated brine (10 mL). The obtained organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained crude product was separated by column chromatography with ethyl acetate / petroleum ether=(1:9) to obtain N,N′-di-tert-butoxycarbonyl-N″- Preparation of phenylguanidine (34 mg, 47% yield).
Embodiment 3
[0031] Preparation of N,N'-di-tert-butoxycarbonyl-N"-(4-methoxy)phenylguanidine
[0032] The structural formula is:
[0033]
[0034] At room temperature, 4-methoxyaniline (24 mg, 0.2 mmol) was dissolved in 3 mL of PhMe solution, and then N, N'-Boc thiourea (66 mg, 0.24 mmol), NIS (5 mg, 0.02 mmol), 70% TBHP (39 mg, 0.3 mmol). After the addition was complete, the reaction was continued at room temperature until TLC showed complete conversion of starting material. Thereafter, the reaction solution was diluted with ethyl acetate (50 ml) and washed three times with saturated brine (10 mL). The obtained organic phase was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the obtained crude product was separated by column chromatography with ethyl acetate / petroleum ether=(1:9) to obtain N,N′-di-tert-butoxycarbonyl-N″- Preparation of phenylguanidine (30 mg, 41% yield).
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