Dimethylformamide → 3-Chloro-5-methylthiophene-2-carbonyl chloride

HRID 844158Notes

Reaction equation

HRID 844158 reaction equation
[C:1]([C:4]1[S:5][C:6]([CH3:10])=[CH:7][C:8]=1[Cl:9])(O)=[O:2].C(Cl)(=O)C([Cl:14])=O.CN(C=O)C>C(Cl)Cl>[Cl:14][C:1]([C:4]1[S:5][C:6]([CH3:10])=[CH:7][C:8]=1[Cl:9])=[O:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 166400013-Chloro-5-methylthiophene-2-carboxylic acid

Product 1

HCID 183768623-Chloro-5-methylthiophene-2-carbonyl chlorideYield 101%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-carboxy-3-chloro-5-methylthiophene (1.2 g, 6.6 mmol) in methylene chloride (16 mL) at 0° C. were added oxalyl chloride (0.6 mL, 7.3 mmol) and a drop of DMF. The mixture was stirred at ambient temperature for 5 hours, then concentrated of all volatiles and dried in vacuo to afford 1.3 g (quantitative yield) of 2-chlorocarbonyl-3-chloro-5-methylthiophene as a pale yellow solid; NMR (DMSO-d6/TFA) 7.4 (s, 1), 2.5 (s, 3) ppm.

Workup

  1. concentrationconcentrated of all volatiles
  2. customdried in vacuo

Sources & evidence

ORD record
ord-3db0c2fe1c4e4c54bc99775bd1bc0d11
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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