Benzo(B)Thiophene → HCID 21316617, compound

HRID 263293Notes

Reaction equation

HRID 263293 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12].[S:15]1[CH:19]=[CH:18][C:17]2[CH:20]=[CH:21][CH:22]=[CH:23][C:16]1=2>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([C:18]2[C:17]3[CH:20]=[CH:21][CH:22]=[CH:23][C:16]=3[S:15][CH:19]=2)=[O:7])=[CH:4][C:3]=1[S:11](=[O:14])(=[O:13])[NH2:12]

Participants

5

Reactant 2

HCID 7221Benzo(B)ThiopheneHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chloride

Product 1

HCID 21316617HCID 21316617, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

5.1 g of powdered 4-chloro-3-sulfamoylbenzoyl chloride are introduced into a solution of 3 g benzo[b]thiophene in 50 ml anhydrous toluene, and subsequently, 12 g titanium tetrachloride are added with agitation. Agitation is continued for 15 minutes at room temperature, the mixture is heated to boiling for about 15 minutes, cooled and poured onto a water/ice suspension. Extraction is carried out then with 70 acetic ester, the organic phase is separated and stirred for 5 hours with an aqueous sodium bicarbonate solution having a pH of 8.5. After separation of the organic phase and drying thereof over magnesium sulfate, the solvent is distilled off and the residue crystallized from toluene. M.p. 154°-156° C.

Workup

  1. temperaturethe mixture is heated
  2. waitto boiling for about 15 minutes
  3. temperaturecooled
  4. extractionExtraction
  5. customwith 70 acetic ester, the organic phase is separated
  6. customAfter separation of the organic phase
  7. customdrying
  8. distillationover magnesium sulfate, the solvent is distilled off
  9. customthe residue crystallized from toluene

Sources & evidence

ORD record
ord-39e98e647f884593abcedb100025b8b7
Source dataset
uspto-grants-1979_05
Patent number
US04156732

Reaction notes

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