Hydrogen Sulfide → 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-carbothioamide

HRID 1414034Notes

Reaction equation

HRID 1414034 reaction equation
[SH2:1].[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[N:4]1[CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24]#[N:25])[CH:22]=2)[NH:17][CH:16]=1.C(N(CC)CC)C.O>CN(C)C=O.CCOCC>[O:12]=[C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:3](=[O:2])[N:4]1[CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([C:24](=[S:1])[NH2:25])[CH:22]=2)[NH:17][CH:16]=1

Participants

7

Reactant 4

HCID 402Hydrogen Sulfide2×HCID 962WaterHCID 8471TriethylamineHCID 103809773-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyl]-1H-indole-5-carbonitrile

Product 1

HCID 202894383-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-carbothioamide

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Hydrogen sulphide gas was passed through a stirred solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-carbonitrile (4 g) and triethylamine (3 ml) in dry dimethylformamide (100 ml) for 6 hours. and the reaction mixture was stirred for a further 7 days. Hydrogen sulphide gas was passed through the reaction mixture for 0.5 hours on each day. Water (200 ml) was added and the mixture was extracted with ethyl acetate (3×200 ml). Evaporation of the washed (H2O) and dried (MgSO4) extracts gave a yellow residue which gave a yellow powder (4.1 g) on trituration with ether. A sample was crystallised from ethanol to give the title compound as yellow microcrystals m.p. 195°-8° C. (dec.)

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×200 ml)
  2. customEvaporation of the
  3. washwashed (H2O)
  4. dry with materialdried (MgSO4)
  5. customextracts gave a yellow residue which

Sources & evidence

ORD record
ord-eed8e9a01c0844e4a83386aaa3235d19
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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