Intermediate for preparing linezolid and preparation method thereof
A technology for linezolid and intermediates, which is applied in the field of intermediates for preparing linezolid, can solve the problems of harsh reaction conditions, low product purity, large amount of solvent and the like, and achieves the use of less solvent amount, high product purity and easy product. Effect
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Embodiment 1
[0039] Preparation of (S)-1-chloro-3-[(3-nitro-E-benzylidene)-amino]-propan-2-ol
[0040]
[0041] Mix m-nitrobenzaldehyde (151g, 1mol), MTBE400ml, ammonia water 27.2g, (S)-epichlorohydrin (93g, 1mol) into the reaction flask, react at room temperature for 20h, separate layers, discard the water layer, and organic The layer was evaporated to dryness to obtain a white solid, which was beaten and washed with n-hexane to obtain the product.
[0042] m / z: 242.05
[0043] Elemental analysis: C, 49.50; H, 4.57; Cl, 14.61; N, 11.54; O, 19.78.
[0044] 1 H NMR: 63.5(d, 1H), 3.58(m, 1H), 3.65(d, 2H), 3.83(d, 2H), 7.78(m, 1H), 8.15(m, 1H), 8.22(m, 1H ), 8.52(s, 1H).
Embodiment 2
[0046] Preparation of (S)-1-chloro-3-[(4-hydroxy-E-benzylidene)-amino]-propan-2-ol
[0047]
[0048] 4-Hydroxybenzaldehyde (122g, 1mol), MTBE300ml, ammonia water 27.2g, (S)-epichlorohydrin (93g, 1mol) were mixed into the reaction flask, after 20h reaction at room temperature, the layers were separated, the aqueous layer was discarded, and the organic The layer was evaporated to dryness to obtain a white solid, which was pulped and washed with petroleum ether to obtain the product.
[0049] m / z: 213.06
[0050] Elemental analysis: C, 56.21; H, 5.66; Cl, 16.59; N, 6.56; O, 14.98
[0051] 1 H NMR: δ3.61(d, 1H), 3.63(m, 1H), 3.715(d, 2H), 3.85(d, 2H), 5.53(s, 1H), 6.85(m, 1H), 6.85(m , 1H), 7.81(m, 1H), 7.81(m, 1H), 8.76(m, 1H).
Embodiment 3
[0053] Preparation of (S)-1-chloro-3-[(2-nitro-E-benzylidene)-amino]-propan-2-ol
[0054]
[0055] Mix 2-nitrobenzaldehyde (151g, 1mol), MTBE400ml, ammonia water 27.2g, (S)-epichlorohydrin (93g, 1mol) into the reaction flask, react at room temperature for 20h, separate layers, discard the water layer, The organic layer was evaporated to dryness to obtain a white solid, which was pulped and washed with n-hexane to obtain the product.
[0056] m / z: 242.05
[0057] Elemental analysis: C, 49.50; H, 4.57; Cl, 14.61; N, 11.54; O, 19.78
[0058] 1 H NMR: δ3.51(d, 1H), 3.58(m, 1H), 3.67(d, 2H), 3.85(d, 2H), 7.59(m, 1H), 7.91(m, 1H), 7.98(m , 1H), 8.09 (m, 1H), 8.76 (s, 1H).
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