Triethylamine → N-[2-(8-chloro-10,11-dihydrodibenz[b,f][1,4]oxazepin-10-yl)-2-oxoethyl]-3-(ethylthio)propanamide
Reaction equation
[CH2:1]([S:3][CH2:4][CH2:5][C:6](Cl)=[O:7])[CH3:2].[NH2:9][CH2:10][C:11]([N:13]1[CH2:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[O:16][C:15]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:14]1=2)=[O:12].C(N(CC)CC)C>C(Cl)Cl>[Cl:28][C:26]1[CH:25]=[CH:24][C:15]2[O:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[CH2:19][N:13]([C:11](=[O:12])[CH2:10][NH:9][C:6](=[O:7])[CH2:5][CH2:4][S:3][CH2:1][CH3:2])[C:14]=2[CH:27]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-(ethylthio)propanoyl chloride (0.87 grams) in methylene chloride (10 mL) was added dropwise to a stirred solution of 10-(aminoacetyl)-8- chloro-10,11-dihydrodibenz-[b,f][1,4]oxazepine (1.50 grams) and triethylamine (0.84 mL) in methylene chloride (40 mL) in an ice bath at 5° C. under nitrogen. The ice bath was removed, and the reaction was stirred for 3 hours. The reaction was diluted with methylene chloride (50 mL) and washed with 50 mL each of 1N HCl, saturated aqueous sodium bicarbonate, and brine. The solution was then dried over MgSO4 and evaporated in vacuo. The yield of the title compound was 1.90 grams (90%). Mp: 148°-151° C.
Workup
- customThe ice bath was removed
- additionThe reaction was diluted with methylene chloride (50 mL)
- washwashed with 50 mL each of 1N HCl, saturated aqueous sodium bicarbonate, and brine
- dry with materialThe solution was then dried over MgSO4
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-09b404f8fcde47f7a35e5411322b5f67
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05212169
Reaction notes
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