Water → 2-chloro-4-(2'-methylpropionamido)-N,N-diethylbenzamide

HRID 359053Notes

Reaction equation

HRID 359053 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].[CH2:17]([NH:19][CH2:20][CH3:21])[CH3:18].O>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])[CH:8]=[CH:7][C:3]=1[C:4]([N:19]([CH2:20][CH3:21])[CH2:17][CH3:18])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 8021DiethylamineHCID 216426352-Chloro-4-(2'-methylpropionamido)benzoyl chloride

Product 1

HCID 191042772-chloro-4-(2'-methylpropionamido)-N,N-diethylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The crude 2-chloro-4-(2'-methylpropionamido)benzoyl chloride from the preceding reaction in dry THF (10 ml) was added dropwise with stirring over 10-15 minutes to a solution of diethylamine (1.46 g) in dry THF (10 ml), at 0°-5° C. After stirring at 0°-10° C. the reaction mixture was stood overnight at room temperature, poured into cold water and extracted with ethyl acetate. This extract was dried and evaporated to give a viscous gum which crystallised slowly and was then recrystallised from ethyl acetate to give 2-chloro-4-(2'-methylpropionamido)-N,N-diethylbenzamide as white crystals (0.507 g).

Workup

  1. additionwas added dropwise
  2. extractionextracted with ethyl acetate
  3. customThis extract was dried
  4. customevaporated
  5. customto give a viscous gum which
  6. customcrystallised slowly
  7. customwas then recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-564217ae25454d86953b67ff684b7e25
Source dataset
uspto-grants-1991_03
Patent number
US04999381

Reaction notes

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