Dimethylformamide → 4-Cyano-2-methylbenzoyl chloride

HRID 572245Notes

Reaction equation

HRID 572245 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[C:5]([CH3:12])[CH:4]=1)#[N:2].S(Cl)([Cl:15])=O.CN(C)C=O>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([Cl:15])=[O:8])=[C:5]([CH3:12])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 118193394-Cyano-2-methylbenzoic acid

Product 1

HCID 866542154-Cyano-2-methylbenzoyl chlorideYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of A-4 (4-cyano-2-methylbenzoic acid) (20 g, 0.124 mol) in toluene (200 mL) was added thionyl chloride (18 mL, 0.248 mol), and catalytic amount of dimethylformamide (0.5 mL). The resultant mixture was stirred at 70° C. for 14 h, and concentrated under reduced pressure to give A-5 (4-cyano-2-methylbenzoyl chloride) (24 g, yield 100%), which was used in the next step without further purification.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6fca3b73700c45acb8b99d9a2e23fdbb
Source dataset
uspto-grants-2015_05
Patent number
US09029402B2

Reaction notes

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