Water → 4,5,6,7-tetrahydro-4-(4-nitrobenzoyl)-8H-thieno[3,2-b]azepin-8-one
Reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3[S:17][CH:18]=[CH:19][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[O-:22]S([O-])(=O)=O.[Mg+2].O.[O-][Mn](=O)(=O)=O.[K+]>CC(C)=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:22])[C:12]3[S:17][CH:18]=[CH:19][C:11]2=3)=[O:9])=[CH:20][CH:21]=1)([O-:3])=[O:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 9.0 g of 4-(4-nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine in 713 ml of acetone is added 6.74 g of MgSO4 and 351 ml of water followed by 8.2 g of KMnO4 and heating at 70° C. for 18 hours. Another 6.24 g of MgSO4 and 8.2 g of KMnO4 is added and heating continued at170° C. for 8 hours. An reaction mixture is filtered through diatomaceous earth and the cake washed with acetone and 500 ml of methylene chloride. The combined filtrates are evaporated in vacuo to a residue which is washed with water and air dried to give 5.7 g of a solids The solid is crystallized from ethyl acetate to give 5.1 g of off white solid, m.p. 184°-186° C.
Workup
- filtrationAn reaction mixture is filtered through diatomaceous earth
- washthe cake washed with acetone and 500 ml of methylene chloride
- customThe combined filtrates are evaporated in vacuo to a residue which
- washis washed with water and air
- customdried
Sources & evidence
- ORD record
- ord-528a6a4078c642d5bf6f69d013561b08
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05654297
Reaction notes
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