Oxalyl chloride → 5-Carboethoxythiophen-2-carbonyl chloride

HRID 129255Notes

Reaction equation

HRID 129255 reaction equation
[C:1]([C:6]1[S:10][C:9]([C:11]([OH:13])=O)=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2].C(Cl)(C([Cl:18])=O)=O>ClCCl.CN(C=O)C>[C:1]([C:6]1[S:10][C:9]([C:11]([Cl:18])=[O:13])=[CH:8][CH:7]=1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 152321235-(Ethoxycarbonyl)thiophene-2-carboxylic acid

Product 1

HCID 102628585-Carboethoxythiophen-2-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of acid 35 (0.64 g, 3.2 mmol) in dichloromethane (20 mL) under argon at room temperature was added a 2.0M solution of (COCl)2 in dichloromethane (2.4 mL, 4.8 mmol) and two drops of DMF, and stirred overnight. Excess (COCl)2 and dichloromethane were removed at reduced pressure, and the viscous, light, yellow product was dried overnight to afford the desired benzoyl chloride 36 as a yellow solid. The structure of the product was also confirmed using IR and 1H NMR spectroscopy.

Workup

  1. customExcess (COCl)2 and dichloromethane were removed at reduced pressure
  2. customthe viscous, light, yellow product was dried overnight

Sources & evidence

ORD record
ord-144f394f694e440780ac1145e4894bb7
Source dataset
uspto-grants-1995_11
Patent number
US05466861

Reaction notes

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