Phenylacetyl chloride → 4,9-Dihydro-9-methyl-4-phenylacetyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one
Reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]2=[CH:13][S:14][CH:15]=[C:4]2[C:3]1=[O:16].[C:17]1([CH2:23][C:24](Cl)=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1C=CC=CC=1>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([C:24](=[O:25])[CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]2=[CH:13][S:14][CH:15]=[C:4]2[C:3]1=[O:16]Participants
4
Procedure
A slurry of 6.90 g. of 4,9-dihydro-9-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one and 4.36 ml. (5.10 g.) of phenylacetyl chloride in 100 ml. of benzene is refluxed with stirring for 5 hours. The reaction mixture is filtered while hot through diatomaceous earth. The filtrate is washed twice with aqueous sodium bicarbonate and dried over magnesium sulfate causing crystals to form. The drying agent and crystals are washed with chloroform and then chloroform:methanol (9:1). The washings are evaporated to residual crystals which are combined twice with ethanol and filtered giving the desired product as tan crystals, mp. 210°-212° C.
Workup
- filtrationThe reaction mixture is filtered while hot through diatomaceous earth
- washThe filtrate is washed twice with aqueous sodium bicarbonate
- dry with materialdried over magnesium sulfate causing crystals
- customto form
- washThe drying agent and crystals are washed with chloroform
- customThe washings are evaporated to residual crystals which
- filtrationfiltered
Sources & evidence
- ORD record
- ord-d2f97491268848b1b581579d7d2cac8e
- Source dataset
- uspto-grants-1979_09
- Patent number
- US04168269
Reaction notes
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