Dimethylformamide → 3-(1-Cyanocyclopropyl)benzoyl chloride

HRID 1874584Notes

Reaction equation

HRID 1874584 reaction equation
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9](O)=[O:10])[CH2:5][CH2:4]1)#[N:2].C(Cl)(=O)C([Cl:18])=O.CN(C)C=O>O1CCCC1>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9]([Cl:18])=[O:10])[CH2:5][CH2:4]1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 574410393-(1-Cyanocyclopropyl)benzoic acid

Product 1

HCID 866319823-(1-Cyanocyclopropyl)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-cyanocyclopropyl)benzoic acid (109 mg, 0.582 mmol) in tetrahydrofuran (5.0 mL) were added oxalyl chloride (62 μL, 0.728 mmol) and N,N-dimethylformamide (about 20 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure to give 3-(1-cyanocyclopropyl)benzoyl chloride as a pale-brown oil.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8ea77ffa375e41889ea914ed4f0e373d
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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