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

HRID 1741218Notes

Reaction equation

HRID 1741218 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

The procedure of Example 13 is followed, but the endcapper is 4-chloro-N,N-dimethylbenzamide (0.20 g, 1.09 mmol) to yield the amido-functionalized macromonomer. 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-ffdaacb215e94d45b495d3fe760774c5
Source dataset
uspto-grants-1999_10
Patent number
US05973075

Reaction notes

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