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

HRID 887914Notes

Reaction equation

HRID 887914 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-cdc65adc94164087acfeb0b9b083e013
Source dataset
uspto-grants-2012_08
Patent number
US08247432B2

Reaction notes

Loading…