Hydrochloric Acid → 4-Chloro-N,N-dimethylbenzamide

HRID 1379172Notes

Reaction equation

HRID 1379172 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH3:11][NH:12][CH3:13].N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:12]([CH3:13])[CH3:11])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 1049PyridineHCID 85014-Chlorobenzoyl chloride

Product 1

HCID 841804-Chloro-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-Chloro-N,N-dimethylbenzamide is prepared by reacting 4-chlorobenzoyl chloride with dimethylamine in toluene with some pyridine (1 mol equivalent per acid chloride) to trap the HCl that is evolved. After aqueous extraction of the pyridinium salt and any excess starting materials, the product is crystallized from the toluene solution.

Workup

  1. extractionAfter aqueous extraction of the pyridinium salt
  2. customany excess starting materials, the product is crystallized from the toluene solution

Sources & evidence

ORD record
ord-ee0d71690e4d4c0b8ab23eb1c1ba4511
Source dataset
uspto-grants-1997_09
Patent number
US05670564

Reaction notes

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