Diphenylacetaldehyde → N-(2,2-Diphenylethenyl)-2-hydroxybenzo(b)thiophene-3-carboxamide

HRID 2231285Notes

Reaction equation

[OH:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([NH2:13])=[O:12].[C:14]1([CH:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>C1(C)C=CC=CC=1>[C:14]1([C:20]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:21][NH:13][C:11]([C:3]2[C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[S:6][C:2]=2[OH:1])=[O:12])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A stirred mixture of 2-hydroxybenzo(b)thiophene-3-carboxamide (0.485 g, 0.0025 m), diphenylacetaldehyde (0.51 g, 0.0026 m), p. toluenesulfonic acid hydrate (30 mg), and dried toluene (15 ml) is set in an oil-bath at 100° C., the bath temperature raised to 150° C., and the mixture heated under reflux until thin-layer chromatography of the mixture indicates completeness of reaction. The cooled reaction mixture is concentrated in vacuo and the residue chromatographed on silica gel (v/v 10-50% CH2Cl2 in hexane) to yield N-(2,2-Diphenylethenyl)-2-hydroxybenzo(b)thiophene-3-carboxamide.

Workup

temperaturethe mixture heated
temperatureunder reflux until thin-layer chromatography of the mixture
customcompleteness of reaction
customThe cooled reaction mixture
concentrationis concentrated in vacuo
customthe residue chromatographed on silica gel (v/v 10-50% CH2Cl2 in hexane)

Sources & evidence

ORD record: ord-c6269d0602b149f0b34ded9210b4f316
Source dataset: uspto-grants-1988_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04782080

Reaction notes

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