Diethyl chlorophosphate → ethyl (2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetate
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH3:15])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[P:16](Cl)([O:21][CH2:22][CH3:23])([O:18][CH2:19][CH3:20])=[O:17]>N1C=CC=CC=1>[CH2:19]([O:18][P:16]([NH:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH3:15])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)([O:21][CH2:22][CH3:23])=[O:17])[CH3:20]Participants
Procedure
To a stirred solution of 4.6 g (0.02 mol) of ethyl 2-(aminothiazol-4-yl)-Z-2-methoxyiminoacetate in 40 ml pyridine at 10°-20° was added 9.0 ml (0.6 mol) diethyl chlorophosphate. The solution was stirred at room temperature for 2 hours. Pyridine was evaporated and the residue was codistilled with benzene and partitioned between water and methylene chloride. The methylene chloride layer was washed with excess 10% aqueous HCl, water, aqueous bicarbonate, saturated sodium chloride, and dried over sodium sulfate. Upon evaporation, 5.5 g brown oil was obtained which was purified on Biosil A using hexane/ethyl acetate (1:4) to afford 2.8 g of yellow crystals, m.p. 96.5-98.0; NMR (300MH2, DCCl3) δ 1.35 (3t, 9, CH3), 3.97 (S, 3, OCH3), 4.17 (q, 4, OCH2), 4.39 (q, 2, OCH2), 6.93 (s, 1, thiazole H).
Workup
- customPyridine was evaporated
- custompartitioned between water and methylene chloride
- washThe methylene chloride layer was washed with excess 10% aqueous HCl, water, aqueous bicarbonate, saturated sodium chloride
- dry with materialdried over sodium sulfate
- customUpon evaporation
Sources & evidence
- ORD record
- ord-6961ae53b84743d283411e8b1dac4ea4
- Source dataset
- uspto-grants-1991_12
- Patent number
- US05077282
Reaction notes
Loading…