Lawesson's reagent → 7-nitro-1H-indole-2-carbothioamide

HRID 1851365Notes

Reaction equation

HRID 1851365 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]([NH2:15])=O)=[CH:9]2)([O-:3])=[O:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:25])=CC=1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13](=[S:25])[NH2:15])=[CH:9]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 473196987-nitro-1H-indole-2-carboxamide

Product 1

HCID 579018667-nitro-1H-indole-2-carbothioamideYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 7-nitro-1H-indole-2-carboxamide (2.50 g), Lawesson's reagent (5.42 g) and tetrahydrofuran (50 mL) was stirred at 50° C. overnight. The reaction mixture was concentrated, and the resulting crystals were filtrated, washed with toluene, and dried to give the title compound (2.08 g, yield 77%) as yellow crystals. melting point>237° C. (decomposition).

Workup

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

Sources & evidence

ORD record
ord-5e685f5067724c0088bef8be3ea2ff52
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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