Diphenylacetaldehyde → 5-fluoro-3-hydroxy-N-(2,2-diphenylethenyl)benzo[b]thiophene-2-carboxamide

HRID 974198Notes

Reaction equation

HRID 974198 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([C:10]([NH2:12])=[O:11])=[C:8]([OH:9])[C:4]=2[CH:3]=1.[C:15]1([CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[F:1][C:2]1[CH:14]=[CH:13][C:5]2[S:6][C:7]([C:10]([NH:12][CH:22]=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:11])=[C:8]([OH:9])[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 13696DiphenylacetaldehydeHCID 54680212HCID 54680212, compound

Product 1

HCID 546802115-fluoro-3-hydroxy-N-(2,2-diphenylethenyl)benzo[b]thiophene-2-carboxamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 5-fluoro-3-hydroxybenzo[b]thiophene-2-carboxamide (400 mg, 1.89 mmol) in hot toluene (35 ml) were added diphenylacetaldehyde (577 mg, 2.84 mmol) and p-toluenesulfonic acid monohydrate (25 mg). The reaction mixture was stirred at reflux temperature for 2 hours with azeotropic removal of water, cooled, and evaporated under diminished pressure. The solid obtained was recrystallized from diethyl ether-hexane to yield 604 mg (82%) of 5-fluoro-3-hydroxy-N-(2,2-diphenylethenyl)benzo[b]thiophene-2-carboxamide, m.p. 186°-189° C.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. customwith azeotropic removal of water
  3. temperaturecooled
  4. customevaporated under diminished pressure
  5. customThe solid obtained
  6. customwas recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-6aac9d44553a4d558f27dd3c96354d30
Source dataset
uspto-grants-1991_11
Patent number
US05068248

Reaction notes

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