N-Acetylsulfanilyl chloride → HCID 20337747, compound

HRID 1395631Notes

Reaction equation

HRID 1395631 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[NH2:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:17]1>N1C=CC=CC=1.C1C=CC=CC=1.C(Cl)(Cl)Cl>[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:15][N:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:17]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3]

Participants

6

Reactant 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 203377683-Phenyl-1H-indol-1-amine

Product 1

HCID 20337747HCID 20337747, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

11.7 G (0.05 mol) of p-acetaminobenzene sulphonyl chloride were added in portions and with stirring to a solution of 15.6 g (0.075 mol) of 1-amino-3-phenyl-indole in 100 ml of pyridine. The temperature of the mixture rose to about 45° C. The mixture was then heated to 60° C. and stirred for 3 hours at this temperature. The red solution obtained was then concentrated by evaporation under vacuum. The viscous, oily residue which was obtained was taken up in a mixture of benzene and chloroform (1:1 by volume) and chromatographically purified through a column of 300 ml Alox Woelm neutral Akt. II. The resulting oily product was crystallised from a little ethanol and was recrystallised from ethanol/water. The crystals of 1-(p-acetaminobenzene sulphonylamino)-3-phenyl-indole melted at 190°-193° C. and were obtained in a yield of 16.5 g (55% of the theoretical).

Workup

  1. customrose to about 45° C
  2. customThe red solution obtained
  3. concentrationwas then concentrated by evaporation under vacuum
  4. customThe viscous, oily residue which was obtained
  5. customchromatographically purified through a column of 300 ml Alox Woelm neutral Akt
  6. customThe resulting oily product was crystallised from a little ethanol
  7. customwas recrystallised from ethanol/water

Sources & evidence

ORD record
ord-ea4b3f82df0d4178ac591cc823b349be
Source dataset
uspto-grants-1980_05
Patent number
US04204998

Reaction notes

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