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

HRID 848568Notes

Reaction equation

HRID 848568 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 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 the 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-aa2d4b3e9a3a4d429dff692b383ab6d9
Source dataset
uspto-grants-1981_10
Patent number
US04296129

Reaction notes

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