Ethyl chloroformate → N-(1-Methyldecyl)-3-(3-Nitrophenyl)-2-butenamide

HRID 1065820Notes

Reaction equation

HRID 1065820 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([CH3:15])=[CH:11][C:12]([OH:14])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].ClC(OCC)=O.[CH3:22][CH:23]([NH2:33])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>ClCCl.C(N(CC)CC)C>[CH3:22][CH:23]([NH:33][C:12](=[O:14])[CH:11]=[C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH3:15])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 1144762-UndecanamineHCID 544021563-(3-Nitrophenyl)-2-butenoic acid

Product 1

HCID 53905448N-(1-Methyldecyl)-3-(3-Nitrophenyl)-2-butenamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Procedure

To a stirred slurry of 5.2 g. of the 3-(3-nitrophenyl)-2-butenoic acid from Preparation 12 having a melting point of 208°-210° C., in 100 ml. of dichloromethane, was added 2.8 g. of triethylamine in 10 ml. of dichloromethane. This was followed by the addition of a solution of 3.0 g. of ethyl chloroformate in 20 ml. of dichloromethane, during 20 minutes. Stirring was continued for 30 minutes, and then a solution of 1-methyldecylamine in 20 ml. of dichloromethane was added dropwise during 25 minutes. Stirring was continued overnight, and the reaction mixture was washed successively with 1 N potassium carbonate, water and saturated sodium chloride. The resulting solution was dried using sodium sulfate, and then it was evaporated in vacuo leaving an oil which solidified on trituration under petroleum ether. This afforded 4.9 g. of the title compound, m.p. 72.5°-74° C.

Workup

  1. additionThis was followed by the addition of a solution of 3.0 g
  2. stirringStirring
  3. waitwas continued overnight
  4. washthe reaction mixture was washed successively with 1 N potassium carbonate, water and saturated sodium chloride
  5. customThe resulting solution was dried
  6. customit was evaporated in vacuo
  7. customleaving an oil which

Sources & evidence

ORD record
ord-c231091e60b4402795c4410a5754cccc
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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