Dimethylformamide → 4-Cyano-2-methylbenzoyl chloride

HRID 238396Notes

Reaction equation

HRID 238396 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-182db5df03a94061a83874a183beea12
Source dataset
uspto-grants-2014_02
Patent number
US08642628B2

Reaction notes

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