Reaction equation
[CH:1]1([C:5]2[N:6]=[C:7](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:30])[CH2:20][C:21]4[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=4[C:23]([OH:25])=O)[CH:15]=[CH:16][CH:17]=3)[S:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.C(OP(Cl)(OCC)=O)C.[CH2:40]([N:42](CC)[CH2:43]C)C.Cl.CNC>O1CCCC1>[CH:1]1([C:5]2[N:6]=[C:7](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:30])[CH2:20][C:21]4[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=4[C:23]([N:42]([CH3:43])[CH3:40])=[O:25])[CH:15]=[CH:16][CH:17]=3)[S:8][CH:9]=2)[CH2:2][CH2:3][CH2:4]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 0.836 g of (E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]benzoic acid, 0.38 g of diethylchlorophosphate, 2.2 g of triethylamine, 1.8 g of dimethylamine hydrochloride and 25 ml of tetrahydrofuran was stored at room temperature for 20 hr. The solvent was removed in vacuo and the residual materials were taken up in 100 ml of methylene chloride and then washed with water (3×30 ml), dried (MgSO4) and the solvent removed in vacuo. The residual materials were crystallized from ethanol to yield (E)-2-[2-[3-[2-[4-(cyclobutyl)-2-thiazolyl]ethenyl]phenylamino]-2-oxoethyl]-N,N-dimethylbenzamide as an off-white colored solid, m.p. 125°-127° C. Anal. Calcd for C26H27N3O2S: C, 70.09; H, 6.11; N, 9.43. Found: C, 69.92; H, 6.25; N, 9.42.
Workup
- customThe solvent was removed in vacuo
- washwashed with water (3×30 ml)
- dry with materialdried (MgSO4)
- customthe solvent removed in vacuo
- customThe residual materials were crystallized from ethanol
Sources & evidence
- ORD record
- ord-a0dd8146b1b74ef988bf2372a0aecc8c
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05273986
Linked notes
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