Cyanamide → 3-(benzenesulfonyl)-5-chloro-N'-cyano-1H-indole-2-carboxamidine

HRID 260496Notes

Reaction equation

HRID 260496 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[NH:15])OCC)=[C:5]2[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17].[N:25]#[C:26][NH2:27]>CO>[C:26]([NH:27][C:11]([C:6]1[NH:7][C:8]2[C:4]([C:5]=1[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:18])=[O:17])=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)=[NH:15])#[N:25]

Participants

4

Reactant 2

HCID 9864CyanamideHCID 135761968Ethyl 5-chloro-3-phenylsulfonylindole-2-carboximidate

Product 1

HCID 1785123053-(benzenesulfonyl)-5-chloro-N'-cyano-1H-indole-2-carboxamidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 5-chloro-3-phenylsulfonylindole-2-carboximidate is reacted with an equimolar amount of cyanamide in absolute methanol (according to the procedure of K. R. Huffman and F. C. Schaefer (J. Org. Chem., 28, 1812 (1963)). After 30-60 minutes the solvent is removed and the residue purified by silica gel chromatography to afford the title compound.

Workup

  1. customAfter 30-60 minutes the solvent is removed
  2. customthe residue purified by silica gel chromatography

Sources & evidence

ORD record
ord-137b4c1d36df4ac9a6d032cd522cafed
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

Loading…