Water → Propanamide, N-(2,5-dichlorophenyl)-2,2-dimethyl-

HRID 2118741Notes

Reaction equation

HRID 2118741 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:3]=1[NH2:4].[C:10](Cl)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12].O>N1C=CC=CC=1>[C:11]([C:10]([NH:4][C:3]1[CH:5]=[C:6]([Cl:9])[CH:7]=[CH:8][C:2]=1[Cl:1])=[O:15])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 962WaterHCID 72622,5-DichloroanilineHCID 62493Pivaloyl chloride

Product 1

HCID 4465103Propanamide, N-(2,5-dichlorophenyl)-2,2-dimethyl-

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 1 kg of 2,5-dichloroaniline in 2500 ml of pyridine is added 840 ml of pivaloyl chloride and the mixture is refluxed for 4 hours. After cooling, the reaction mixture is poured into water. The solid is filtered, washed with water and air dried to yield N-tert-butylcarbonyl-2,5-dichloroaniline, melting at 74°-76°.

Workup

  1. temperaturethe mixture is refluxed for 4 hours
  2. temperatureAfter cooling
  3. filtrationThe solid is filtered
  4. washwashed with water and air
  5. customdried

Sources & evidence

ORD record
ord-1073eb3c3e3447cbb7dfe55330b4ac9e
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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