Dimethylamine → N-(2-nitrophenyl)-2-dimethylaminoacetamide

HRID 1415634Notes

Reaction equation

HRID 1415634 reaction equation
[CH3:1][NH:2][CH3:3].[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:17])[CH2:15]Cl)([O-:6])=[O:5]>C(O)C>[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:17])[CH2:15][N:2]([CH3:3])[CH3:1])([O-:6])=[O:5]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 2224432-chloro-N-(2-nitrophenyl)acetamide

Product 1

HCID 2958870N-(2-nitrophenyl)-2-dimethylaminoacetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of dimethylamine in ethanol (40 ml. of a 33% w/w solution) was added to a suspension of N-(2-nitrophenyl)-2-chloroacetamide (14.9 g) [prepared by the method described by G. Tennant, J.C.S., (1963), 2428] in ethanol (70 ml) and the mixture was heated to reflux, with stirring, for 2hours. After cooling, the ethanol and excess dimethylamine were evaporated off under reduced pressure and the solid residue was treated with an aqueous potassium hydroxide solution (100 ml., 40% w/v). The resulting suspension was extracted with diethyl ether (3 × 100 ml) and the combined extracts dried over magnesium sulphate and evaporated to give N-(2-nitrophenyl)-2-dimethylaminoacetamide (13.8 g), m.p. 44°-47° C., sufficiently pure to be used in the next stage of the synthesis, the preparation of N-(2-aminophenyl)-2-dimethylaminoacetamide.

Workup

  1. customprepared by the method
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. customthe ethanol and excess dimethylamine were evaporated off under reduced pressure
  5. additionthe solid residue was treated with an aqueous potassium hydroxide solution (100 ml., 40% w/v)
  6. extractionThe resulting suspension was extracted with diethyl ether (3 × 100 ml)
  7. dry with materialthe combined extracts dried over magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-302f9863ddcd4d049d931e62a93e2b9d
Source dataset
uspto-grants-1977_01
Patent number
US04005217

Reaction notes

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