Dimethylformamide → 3-(1-Cyanocyclopropyl)benzoyl chloride

HRID 1800416Notes

Reaction equation

HRID 1800416 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 (139 mg, 0.742 mmol) produced in Example B3(ii) in tetrahydrofuran (7.0 mL) were added oxalyl chloride (80 μL, 0.929 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-93a3e83951064ed68cfe44a5e4996f65
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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