Acetic Acid → HCID 790201, compound

HRID 1873674Notes

Reaction equation

HRID 1873674 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]#[N:12])=[CH:2]1.[S:13]1C=CC=C1CC(O)=O.C(O)(=O)C>CCOC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([NH2:12])=[S:13])=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 159702-Thiopheneacetic acidHCID 351795Indole-3-acetonitrile

Product 1

HCID 790201HCID 790201, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (1H-indol-3-yl)-acetonitrile (5.0 g, 32 mmol), thiolacetic acid (6.8 mL, 96 mmol) and glacial acetic acid (25 mL) was heated at 100° C. for 4 h. After cooling to room temperature the reaction mixture was diluted with EtOAc, washed with water twice and brine. The organics were then concentrated under vacuum and purified by column chromatography (SiO2, EtOAc/hexanes) to afford 2-(1H-indol-3-yl)-thioacetamide as an orange solid (2.9 g, 48%).

Workup

  1. washwashed with water twice
  2. concentrationThe organics were then concentrated under vacuum
  3. custompurified by column chromatography (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-6b48ab5586b2467e8f993ce0f5ec7dfb
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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