Hydrogen Sulfide → 3-[2-(Dimethylamino)ethyl]-1H-indole-5-carbothioamide

HRID 1762483

Reaction equation

HRID 1762483 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[NH:7][CH:6]=1.C(N(CC)CC)C.[SH2:24]>CN(C)C=O>[CH3:16][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14](=[S:24])[NH2:15])[CH:12]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 28511Indole-5-carbonitrile, 3-(2-dimethylaminoethyl)-

Product 1

HCID 200413563-[2-(Dimethylamino)ethyl]-1H-indole-5-carbothioamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-[2-(dimethylamino)ethyl]-1H-indole-5-carbonitrile (13.0 g) and triethylamine (50 ml) in dimethylformamide (300 ml) was stirred for 2 h whilst gaseous hydrogen sulphide was bubbled through it. More triethylamine (10 ml) was added and the solution was stirred at room temperature for 2 days, then evaporated in vacuo to give an oil (15 g) which was partitioned between ethyl acetate (500 ml) and water (3×250 ml). The organic layer was dried (MgSO4) pre-absorbed onto silica and purified by flash chromatography (A). The appropriate fractions were combined, concentrated in vacuo and triturated with ether (250 ml) to give the title compound (12.0 g) as a solid, m.p. 155°.

Workup

  1. customwas bubbled through it
  2. additionMore triethylamine (10 ml) was added
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-2faf13d4fbc9489b9d679b30d03af470
Source dataset
uspto-grants-1989_05
Patent number
US04833153

Linked notes

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