Hydrochloric Acid → 2-(4-Chloro-3-sulfamoylbenzoyl)-benzo[b]furan

HRID 263297

Reaction equation

HRID 263297 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([S:12](=[O:15])(=[O:14])[NH2:13])[CH:6]=1)=[O:4].[CH:16](=O)[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[OH:19].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([C:2]2[O:19][C:18]3[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=3[CH:16]=2)=[O:4])=[CH:6][C:7]=1[S:12](=[O:15])(=[O:14])[NH2:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 12952390Bromo-4'-chloro-3'-sulfamoylacetophenone

Product 1

HCID 213165932-(4-Chloro-3-sulfamoylbenzoyl)-benzo[b]furan

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 g 2-Bromo-4'-chloro-3'-sulfamoylacetophenone and 1.63 g salicylaldehyde are maintained for 2 hours with agitation and with exclusion of moisture at a temperature of 80° C. in 50 ml anhydrous dimethyl formamide, in the presence of 2.9 g potassium carbonate ground under anhydrous conditions. After cooling, the batch is poured into a mixture of icewater and excess hydrochloric acid, extracted with ethyl acetate and dried over sodium sulfate. After having distilled off the solvent, crystallization is carried out from di-isopropyl ether and isopropanol. M.p. 152°-156° C. Recrystallization from glacial acetic acid after clarification with active charcoal gives colorless crystals having a melting point of 167°-170° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. distillationAfter having distilled off
  5. customthe solvent, crystallization
  6. customRecrystallization from glacial acetic acid after clarification with active charcoal
  7. customgives colorless crystals

Sources & evidence

ORD record
ord-be87ce7bc2cb4532b71c9d0edfccb620
Source dataset
uspto-grants-1979_05
Patent number
US04156732

Linked notes

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