Triethylamine → 2-chloro-(2',2'-dimethylpropionamido)-N,N-dimethylbenzamide

HRID 1198202Notes

Reaction equation

HRID 1198202 reaction equation
N[C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=[O:7])=[C:4]([Cl:13])[CH:3]=1.C([N:16](CC)CC)C.[CH3:21][C:22]([CH3:27])([CH3:26])[C:23](Cl)=[O:24]>C(Cl)Cl>[Cl:13][C:4]1[C:3]([NH:16][C:23](=[O:24])[C:22]([CH3:27])([CH3:26])[CH3:21])=[CH:2][CH:12]=[CH:11][C:5]=1[C:6]([N:8]([CH3:10])[CH3:9])=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 109434804-amino-2-chloro-N,N-dimethylbenzamide

Product 1

HCID 541259092-chloro-(2',2'-dimethylpropionamido)-N,N-dimethylbenzamideYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Amino-2-chloro-N,N-dimethylbenzamide (1.0 g) and triethylamine (1.21 g) were dissolved in methylene chloride (20 ml) and the solution was cooled to 0°-5° C. 2,2-Dimethylpropionyl chloride (1.21 g) was added dropwise keeping the temperature below 100° C. and the resulting orange solution stirred at 0°-10° C. for 0.5 hour. The organic solution was then washed with aqueous sodium bicarbonate and then water, dried and evaporated to give an orange solid. This was recrystallised from 3:1 ethyl acetate:chloroform to give 2-chloro-(2',2'-dimethylpropionamido)-N,N-dimethylbenzamide as an off-white crystalline solid (1.027 g), m.p. 202°-203° C.

Workup

  1. temperaturethe solution was cooled to 0°-5° C
  2. customthe temperature below 100° C.
  3. washThe organic solution was then washed with aqueous sodium bicarbonate
  4. dry with materialwater, dried
  5. customevaporated
  6. customto give an orange solid
  7. customThis was recrystallised from 3:1 ethyl acetate

Sources & evidence

ORD record
ord-c483d589f31c4b66af22eaa908cd427e
Source dataset
uspto-grants-1994_01
Patent number
US05280044

Reaction notes

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