Hydrogen Sulfide → 1-Acetyl-2,3-dihydro-1H-indole-2-carbothioamide

HRID 551392Notes

Reaction equation

HRID 551392 reaction equation
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13]#[N:14])(=[O:3])[CH3:2].C(N(CC)CC)C.[SH2:22]>N1C=CC=CC=1>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH:5]1[C:13](=[S:22])[NH2:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 148193141-Acetyl-2,3-dihydro-1H-indole-2-carbonitrile

Product 1

HCID 219141121-Acetyl-2,3-dihydro-1H-indole-2-carbothioamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1-acetyl-2,3-dihydro-1H-indole-2-carbonitrile (0.00988 mol) and Triethylamine (0.0197 mol) in pyridine (50 ml) was treated with hydrogen sulfide (gas) at room temperature via a bubbler for 2 hours and the resultant saturated reaction mixture was closed and allowed to set for 16 hours. The reaction mixture was poured into 200 ml of an ice water slurry. A voluminous precipitate formed. The mixture was recooled in an ice bath and the precipitate was collected by suction filtration, washed with cold water, and air dried, yielding 1.62 g of 1-acetyl-2,3-dihydro-1H-indole-2-carbothioamide (intermediate 13, mp. 194-195° C.).

Workup

  1. customthe resultant saturated reaction mixture was closed
  2. customA voluminous precipitate formed
  3. customThe mixture was recooled in an ice bath
  4. filtrationthe precipitate was collected by suction filtration
  5. washwashed with cold water, and air
  6. customdried

Sources & evidence

ORD record
ord-51e06ed143f74b3199050316cc7c01ec
Source dataset
uspto-grants-2011_05
Patent number
US07947713B2

Reaction notes

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