3-Benzenesulfonyl-5-chloroindole-2-carboxamide → 5-Chloro-3-phenylsulfonylindole-2-thiocarboxamide

HRID 260475Notes

Reaction equation

HRID 260475 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]([NH2:13])=O)=[C:5]2[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].COC1C=CC(P2SP(C3C=CC(OC)=CC=3)[S:32]2)=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[S:32])[NH2:13])=[C:5]2[S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15]

Participants

3

Reactant 2

HCID 4548443-Benzenesulfonyl-5-chloroindole-2-carboxamideHCID 127328752,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane

Product 1

HCID 224014745-Chloro-3-phenylsulfonylindole-2-thiocarboxamide

Procedure

Reaction of 5-chloro-3-phenylsulfonylindole-2-carboxamide with 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane (Lawesson's reagent) according to the procedure of Example 18 gave the title compound. Chromatographic purification on silica gel was carried out using 30% ethyl acetate-methylene chloride, followed by 50% ethyl acetate-methylene chloride. The pure product had mp 207°-210° C. Anal. calcd for C15H11ClN2O2S2 : C, 51.35; H, 3.16; N, 7.98. Found: C, 50.84; H, 3.08; N, 8.04. NMR (DMSO-d6) δ12.90 (1H, s), 10.71 (1H, s), 10.70 (1H, s), 8.0-8.6 (2H, m), 7.84 (1H, d, J=2 Hz), 7.54-7.66 (3H, m), 7.46 (1H, d, J=8.5 Hz), 7.30 (1H, dd, J=8.5, 2 Hz).

Sources & evidence

ORD record
ord-7df790cfa0a2455e8eceba588672c709
Source dataset
uspto-grants-1996_06
Patent number
US05527819

Reaction notes

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