Hydrochloric Acid → 4-Formyl-N-[4-(trifluoromethoxy)phenyl]benzene-1-sulfonamide

HRID 1696615Notes

Reaction equation

HRID 1696615 reaction equation
Cl[S:2]([C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[F:13][C:14]([F:24])([F:23])[O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.N1C=CC=CC=1.Cl>ClC(Cl)C>[CH:9]([C:8]1[CH:11]=[CH:12][C:5]([S:2]([NH:20][C:19]2[CH:21]=[CH:22][C:16]([O:15][C:14]([F:13])([F:23])[F:24])=[CH:17][CH:18]=2)(=[O:4])=[O:3])=[CH:6][CH:7]=1)=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6008484-(Trifluoromethoxy)anilineHCID 27592104-Formylbenzene-1-sulfonyl chloride

Product 1

HCID 714239844-Formyl-N-[4-(trifluoromethoxy)phenyl]benzene-1-sulfonamideYield 46.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

to a mixture of 610 mg of 4-chlorosulfonylbenzaldehyde (3 mmoles) and 460 mg of 4-trifluoromethoxyaniline (3 mmoles) in 2 ml of dichloroethane is added 2 ml of pyridine (25 mmoles). The reaction mixture is stirred at room temperature for 5 hours and then poured into 100 ml of 10% HCl solution. The mixture is extracted twice with 30 ml of DCM. The combined organic extracts are washed with 30 ml of water, 30 ml of a saturated solution of sodium bicarbonate and brine, and the solution is dried over MgSO4 and concentrated. The crude product is purified on silica gel using DCM/AcOEt 90/10 as eluent. 0.48 g of 4-formyl-N-(4-trifluoromethoxy-phenyl)-benzenesulfonamide is isolated as a white solid (yield=47%). Analytical LC/MS method A:([M+H]+): 346, RT: 5.53 min (gradient 5 to 85% acetonitrile in 7 min).

Workup

  1. extractionThe mixture is extracted twice with 30 ml of DCM
  2. washThe combined organic extracts are washed with 30 ml of water, 30 ml of a saturated solution of sodium bicarbonate and brine
  3. dry with materialthe solution is dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product is purified on silica gel

Sources & evidence

ORD record
ord-5487a8715ad746b0992cb861cd8ae5fc
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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