Triethylamine → 2-chloro-4-(3'-chloro-2',2'-dimethylpropionamido)-N,N-dimethylbenzamide

HRID 1198206Notes

Reaction equation

HRID 1198206 reaction equation
[Cl:1][CH2:2][C:3]([CH3:8])([CH3:7])[C:4](Cl)=[O:5].[NH2:9][C:10]1[CH:20]=[CH:19][C:13]([C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[C:12]([Cl:21])[CH:11]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:21][C:12]1[CH:11]=[C:10]([NH:9][C:4](=[O:5])[C:3]([CH3:8])([CH3:7])[CH2:2][Cl:1])[CH:20]=[CH:19][C:13]=1[C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 613453-Chloro-2,2-dimethylpropanoyl chlorideHCID 109434804-amino-2-chloro-N,N-dimethylbenzamide

Product 1

HCID 539806102-chloro-4-(3'-chloro-2',2'-dimethylpropionamido)-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Chloro-2,2-dimethylpropionyl chloride (1.86 g) was added dropwise over 5 minutes to 4-amino-2-chloro-N,N-dimethylbenzamide (2.00 g) suspended in dry methylene chloride (40 ml) and dry triethylamine (1.21 g) with stirring, keeping the temperature below 10° C. After stirring for 1 hour and warming to room temperature, methylene chloride (40 ml) was added and the solution washed with 2M hydrochloric acid, saturated aqueous sodium bicarbonate and then saturated brine. The solution was then dried and evaporated to yield a sticky yellow solid which was recrystallised from ethyl acetate/chloroform to give 2-chloro-4-(3'-chloro-2',2'-dimethylpropionamido)-N,N-dimethylbenzamide, as a white crystalline solid (2.349 g) m.p. 179°-181° C.

Workup

  1. customthe temperature below 10° C
  2. washthe solution washed with 2M hydrochloric acid, saturated aqueous sodium bicarbonate
  3. customThe solution was then dried
  4. customevaporated
  5. customto yield a sticky yellow solid which
  6. customwas recrystallised from ethyl acetate/chloroform

Sources & evidence

ORD record
ord-3cef67425c9c4c1dac1845ae0259f13c
Source dataset
uspto-grants-1994_01
Patent number
US05280044

Reaction notes

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