Oxalyl chloride → 5-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carbonyl-chloride

HRID 1977358Notes

Reaction equation

HRID 1977358 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7]([C:9]1[S:13][C:12]([C:14](O)=[O:15])=[CH:11][CH:10]=1)=[O:8].C(Cl)(=O)C([Cl:24])=O>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:5][NH:6][C:7]([C:9]1[S:13][C:12]([C:14]([Cl:24])=[O:15])=[CH:11][CH:10]=1)=[O:8]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 186171155-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carboxylic acid

Product 1

HCID 186171255-(3,4-Dichlorobenzyl-carbamoyl)-thiophene-2-carbonyl-chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirring solution of (12(b)) (495 mg; 1.5 mmole) in dichloromethane (25 mL) was cooled in an ice bath and DMF (1 drop) and oxalyl chloride (0.175 mL; 2.0 mmole) added dropwise. The solution was stirred at ambient temperature under argon for 4 hours. The dichloromethane and excess oxalyl chloride were removed in vacuo. The residue was azeotroped uith toluene (2×15 mL) to give 5-(3,4-dichlorobenzyl-carbamoyl)-thiophene-2-carbonyl-chloride (12(c)) which was used crude in the next step.

Workup

  1. customThe dichloromethane and excess oxalyl chloride were removed in vacuo
  2. customThe residue was azeotroped uith toluene (2×15 mL)

Sources & evidence

ORD record
ord-c40991672c294059942cac1dbff3f3dd
Source dataset
uspto-grants-2001_05
Patent number
US06232338B1

Reaction notes

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