Dimethylformamide → 1H-indole-2-carbonyl Chloride

HRID 258109Notes

Reaction equation

HRID 258109 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=O.CN(C)C=O.S(Cl)([Cl:20])=O>ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([Cl:20])=[O:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 72899Indole-2-carboxylic acid

Product 1

HCID 118162081H-indole-2-carbonyl Chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of indole-2-carboxylic acid (2.18 g), N,N-dimethylformamide (52 mg) and thionyl chloride (1.0 ml) in dry dichloromethane (22 ml) was refluxed for 1 hour to give a solution of 2-indolylcarbonyl chloride.

Workup

  1. temperaturewas refluxed for 1 hour

Sources & evidence

ORD record
ord-47d4ab4a1d1343a3b30f1c071df0524a
Source dataset
uspto-grants-1993_11
Patent number
US05264433

Reaction notes

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