Tetrahydrofuran → trans-N-(1-Methyldecyl)-2-(4-nitrophenyl)cyclopropanecarboxamide

HRID 1065826Notes

Reaction equation

HRID 1065826 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[CH2:12][C@H:11]2[C:13]([OH:15])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O1CCCC1.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]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:27][CH:28]([NH:38][C:13]([C@@H:11]1[CH2:12][C@H:10]1[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)=[O:15])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10928Ethyl chloroformateHCID 1144762-UndecanamineHCID 12854631rac-(1R,2R)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid

Product 1

HCID 54327360trans-N-(1-Methyldecyl)-2-(4-nitrophenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
5 °C

Procedure

To a stirred slurry of 2.1 g. of trans-2-(4-nitrophenyl)cyclopropanecarboxylic acid in 30 ml. of tetrahydrofuran was added 1.1 g. of triethylamine. The clear solution thus obtained was cooled to ca. 5° C., and a solution of 1.2 g. of ethyl chloroformate in 5 ml. of chloroform was added dropwise, with stirring, during 15 minutes. Stirring was continued for 20 minutes, and then a solution of 1.9 g. of 1-methyldecylamine in 5 ml. of chloroform was added dropwise during 15 minutes. The cooling bath was removed, and stirring was continued for 1 hour. At this point the solvent was removed in vacuo and the residue was triturated with ether. The solid which remained out of solution was removed by filtration and discarded. The ether was evaporated in vacuo, and the residue was recrystallized from a 1:1 mixture of isopropanol and petroleum ether. This afforded 2.9 g. of the title compound as a waxy solid.

Workup

  1. customThe clear solution thus obtained
  2. stirringStirring
  3. waitwas continued for 20 minutes
  4. customThe cooling bath was removed
  5. stirringstirring
  6. waitwas continued for 1 hour
  7. customAt this point the solvent was removed in vacuo
  8. customthe residue was triturated with ether
  9. customwas removed by filtration
  10. customThe ether was evaporated in vacuo
  11. customthe residue was recrystallized from a 1:1 mixture of isopropanol and petroleum ether

Sources & evidence

ORD record
ord-d2281d6a743b4a16b92ceb5c6707d170
Source dataset
uspto-grants-1982_05
Patent number
US04331683

Reaction notes

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