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

HRID 263284

Reaction equation

HRID 263284 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].ClC1C=CC(C(O)=O)=CC=1S(=O)(=O)N.S(Cl)(Cl)=O.[CH2:33]([C:35]1[O:39][C:38]2[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=2[CH:36]=1)[CH3:34].[Cl-].[Al+3].[Cl-].[Cl-].Cl>ClC1C=CC=CC=1>[CH2:33]([C:35]1[O:39][C:38]2[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=2[C:36]=1[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[C:3]([S:11](=[O:14])(=[O:13])[NH2:12])[CH:4]=1)[CH3:34]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 145684-Chloro-3-sulfamoylbenzoic acidHCID 24386Thionyl ChlorideHCID 765822-EthylbenzofuranHCID 30179793-(Aminosulfonyl)-4-chlorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 213165862-Ethyl-3-(4-chloro-3-sulfamoylbenzoyl)-benzo[b]furan

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
0 °C

Procedure

10 mg of powdered 4-chloro-3-sulfamoylbenzoyl chloride (melting point, m.p. 166° C.), prepared from 4-chloro-3-sulfamoylbenzoic acid and thionyl chloride, are introduced into 70 ml of anhydrous chlorobenzene, subsequently 6.32 g of 2-ethylbenzo[b]furan are added, and the reaction mixture is cooled to 0° C. After addition of 11.4 g of anhydrous aluminum chloride, the reaction batch is maintained at a temperature of 5° to 10° C., subsequently stirred for 5 hours at 15° C., and the mixture is then poured into a suspension of 200 g of ice and 10 ml of concentrated hydrochloric acid. After extraction with ethyl acetate and washing with water, the organic phase is stirred for 6 hours with a dilute NaHCO3 solution having a pH of 8.5, dried over magnesium sulfate, and, after evaporation, a light yellow to colorless viscous oil is obtained which crystallizes from petroleum ether. Colorless crystals, m.p. 170°-172° C. (from a small amount of methanol).

Workup

  1. additionare added
  2. temperaturethe reaction batch is maintained at a temperature of 5° to 10° C.
  3. extractionAfter extraction with ethyl acetate
  4. washwashing with water
  5. stirringthe organic phase is stirred for 6 hours with a dilute NaHCO3 solution
  6. dry with materialdried over magnesium sulfate
  7. customafter evaporation
  8. customa light yellow to colorless viscous oil is obtained which
  9. customcrystallizes from petroleum ether

Sources & evidence

ORD record
ord-9b94943a4cff48128432d38db0f93c8b
Source dataset
uspto-grants-1979_05
Patent number
US04156732

Linked notes

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