Water → 4,5,6,7-tetrahydro-4-(4-nitrobenzoyl)-8H-thieno[3,2-b]azepin-8-one

HRID 862991Notes

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

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 at 70° C. for 8 hours. An additional 6.24 g of MgSO4 and 8.2 g of KMnO4 is added and heating continued at 70° C. for 18 hours. The 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 solid. The solid is crystallized from ethyl acetate to give 5.1 g of off white solid, m.p. 184°-186° C.

Workup

temperatureheating
temperatureheating
waitcontinued at 70° C. for 18 hours
filtrationThe 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-ae9b312725944fd5a52eb404fef17051
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05719278

Reaction notes

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