Lawesson's reagent → 6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamide

HRID 1994726Notes

Reaction equation

HRID 1994726 reaction equation
[Cl:1][C:2]1[C:10]([NH:11][S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:20]([NH2:22])=O)[NH:8]2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:32])=CC=1>O1CCCC1>[Cl:1][C:2]1[C:10]([NH:11][S:12]([C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)(=[O:14])=[O:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:20](=[S:32])[NH2:22])[NH:8]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 574760286-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide

Product 1

HCID 574760296-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carbothioamideYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-chloro-7-[(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (0.80 g), Lawesson's reagent (0.90 g) and tetrahydrofuran (15 ml) was stirred at 60° C. for 3 hr. The reaction mixture was concentrated, toluene was added, and the resulting crystals were filtrated, washed with toluene, and dried to give the title compound (0.75 g, yield 91%) as yellow crystals. melting point 228-230° C. (decomposition).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiontoluene was added
  3. filtrationthe resulting crystals were filtrated
  4. washwashed with toluene
  5. customdried

Sources & evidence

ORD record
ord-c71374e529ae44998cfca93985eb4777
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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