Ethyl chloroformate → N-(1-Methyldecyl)-3-phenyl-3-(4-nitrophenyl)propenamide

HRID 66620Notes

Reaction equation

HRID 66620 reaction equation
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:8][C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(OCC)=O.[CH3:27][CH:28]([NH2:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>>[CH3:27][CH:28]([NH:38][C:9](=[O:11])[CH:8]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 3

HCID 10928Ethyl chloroformateHCID 1144762-UndecanamineHCID 534276003-(4-Nitrophenyl)-3-phenylprop-2-enoic acid

Product 1

HCID 53836625N-(1-Methyldecyl)-3-phenyl-3-(4-nitrophenyl)propenamideYield 51%

Procedure

The title compound was prepared from 3-phenyl-3-(4-nitrophenyl)propenoic acid via mixed anhydride formation using ethyl chloroformate, followed by reaction with 1-methyldecylamine, substantially according to the procedure of Preparation 21. The product was induced to solidify by trituration under hexane. The solid was recrystallized from hexane, giving a small amount of material which was discarded. The mother liquors were evaporated in vacuo to give an oil which solidified when stirred under acetonitrile. The solid was filtered off, giving a 51% yield of the title compound, m.p. 69°-71° C.

Workup

  1. customsubstantially according to the procedure of Preparation 21
  2. customThe solid was recrystallized from hexane
  3. customgiving a small amount of material which
  4. customThe mother liquors were evaporated in vacuo
  5. customto give an oil which
  6. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-ca363b7f65534cd6b1c78e535ccde923
Source dataset
uspto-grants-1982_08
Patent number
US04342781

Reaction notes

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