Sodium Hydroxide → 10,11-Dihydro-2-methylsulfonyl-11-oxodibenzo[b,f]thiepin
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:18][C:19]([OH:21])=O)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[OH-].[Na+]>>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:18][C:19](=[O:21])[C:9]=2[CH:10]=1)(=[O:3])=[O:4]Participants
3
Procedure
A mixture of 1.0 g of 2-(4-methylsulfonylphenylthio)phenylacetic acid and 10 ml of polyphosphoric acid under nitrogen is stirred at 90°-100° C. for 2 hours. The reaction mixture is permitted to cool and then poured into 100 ml of an ice-water slurry. The aqueous solution is basified with 20% sodium hydroxide before being extracted with methylene chloride. The combined extracts are dried and then evaporated to dryness leaving an oil. The oil is chromatographed through a silica gel column with a 2% methanol in methylene chloride eluant. The chromatographed solution is evaporated to dryness providing 10,11-dihydro-2-methylsulfonyl-11-oxodibenzo[b,f]thiepin.
Workup
- temperatureto cool
- extractionbefore being extracted with methylene chloride
- customThe combined extracts are dried
- customevaporated to dryness
- customleaving an oil
- customThe oil is chromatographed through a silica gel column with a 2% methanol in methylene chloride eluant
- customThe chromatographed solution is evaporated to dryness
Sources & evidence
- ORD record
- ord-ad9f4a329b9d49bb9722f5c66efbce7e
- Source dataset
- uspto-grants-1988_10
- Patent number
- US04775683
Reaction notes
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