Acetic Acid → N-(7-Oxo-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)formamide
Reaction equation
[CH:1]([NH:3][CH:4]1[C:12]2[CH:11]=[CH:10][S:9][C:8]=2[CH2:7][CH2:6][CH2:5]1)=[O:2].[Cl-].[Na+].C(O)(=[O:17])C>>[CH:1]([NH:3][CH:4]1[C:12]2[CH:11]=[CH:10][S:9][C:8]=2[C:7](=[O:17])[CH2:6][CH2:5]1)=[O:2]Participants
Procedure
A solution of N-formyl-4,5,6,7tetrahydrobenzo[b]thiophen-4-amine (60 g) in 50% aqueous acetic acid (1,112 ml) is stirred and ceric ammonium nitrate (727 g) is added over 20-25 minutes at 25° to 30° C. The mixture is stirred at room temperature for 15 minutes, saturated with sodium chloride and extracted with methylene chloride (2 × 770 and 1 × 400 ml). The combined methylene chloride extracts are washed with brine (380 ml) and then with water (155 ml). The water wash is extracted with methylene chloride (155 ml) and this extract is combined with the main methylene chloride extract. The methylene chloride is evaporated and the residue is triturated with ether (250 ml), collected and washed with ether to afford the title formamide, m.p. 104° to 110° C.
Workup
- extractionextracted with methylene chloride (2 × 770 and 1 × 400 ml)
- washThe combined methylene chloride extracts are washed with brine (380 ml)
- washThe water wash
- extractionis extracted with methylene chloride (155 ml)
- extractionextract
- customThe methylene chloride is evaporated
- customthe residue is triturated with ether (250 ml)
- customcollected
- washwashed with ether
Sources & evidence
- ORD record
- ord-91b73b0f4d394ee2af1d41da62d389db
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03994924
Reaction notes
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