Dimethylformamide → 3-Cyano-4-[(cyclopropylmethyl)oxy]benzoyl chloride

HRID 2192481Notes

Reaction equation

HRID 2192481 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[C:7]([C:9]1[CH:10]=C([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH:20]1[CH2:22][CH2:21]1)C(O)=O)#[N:8].CN(C)C=O>ClCCl>[C:7]([C:9]1[CH:10]=[C:1]([CH:15]=[CH:16][C:17]=1[O:18][CH2:19][CH:20]1[CH2:22][CH2:21]1)[C:2]([Cl:4])=[O:3])#[N:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 668780013-Cyano-4-(cyclopropylmethoxy)benzoic acid

Product 1

HCID 866511443-Cyano-4-[(cyclopropylmethyl)oxy]benzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (0.040 ml, 0.460 mmol) was added to a stirred solution of 3-cyano-4-[(cyclopropylmethyl)oxy]benzoic acid (D24; 50 mg, 0.230 mmol) in dichloromethane (DCM) (2 ml) containing N,N-dimethylformamide (DMF) (0.02 ml) at room temperature under nitrogen, and the mixture was stirred at room temperature for 2 h. The solvent was evaporated in vacuo to give the title compound (54.2 mg) which was used in the subsequent step (D49) without purification.

Workup

  1. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-1dac3804346d462588f7baebeedbc12d
Source dataset
uspto-grants-2012_12
Patent number
US08329730B2

Reaction notes

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