Dimethylamine → N-(4-butyl-2-nitrophenyl)-2-(dimethylamino)acetamide

HRID 1415643Notes

Reaction equation

HRID 1415643 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:15])[CH2:13]Br)=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)[CH2:2][CH2:3][CH3:4].[CH3:19][NH:20][CH3:21]>C(O)C>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:15])[CH2:13][N:20]([CH3:21])[CH3:19])=[C:7]([N+:16]([O-:18])=[O:17])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 21482995N-(4-n-butyl-2-nitrophenyl)-2-bromoacetamide

Product 1

HCID 21482988N-(4-butyl-2-nitrophenyl)-2-(dimethylamino)acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A suspension of N-(4-n-butyl-2-nitrophenyl)-2-bromoacetamide (41 g) in ethanol (200 ml) was treated with a solution of dimethylamine in ethanol (90 ml of 20% w/w). The mixture was refluxed for one hour and the ethanol was evaporated off. Water (100 ml) was added and the mixture extracted with diethyl ether (3 × 200 ml). The extract was dried over magnesium sulphate, filtered and evaporated to give N-(4-n-butyl-2-nitrophenyl)-2-dimethylaminoacetamide as a yellow oil which was used without further purification in the next stage.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. customthe ethanol was evaporated off
  3. additionWater (100 ml) was added
  4. extractionthe mixture extracted with diethyl ether (3 × 200 ml)
  5. dry with materialThe extract was dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-a8c4d1c2cf4b458dbbf5cebc50591543
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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