Triethylamine → HCID 10220070, compound

HRID 1197016Notes

Reaction equation

HRID 1197016 reaction equation
[F:1][C:2]1[CH:3]=[C:4](/[C:8](/[CH3:13])=[CH:9]/[C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.C(Cl)(=O)OCC(C)C.[CH:29]1([NH2:32])[CH2:31][CH2:30]1>C1(C)C=CC=CC=1>[CH:29]1([NH:32][C:10](=[O:12])/[CH:9]=[C:8](/[C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)\[CH3:13])[CH2:31][CH2:30]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 69828CyclopropylamineHCID 15020106HCID 15020106, compound

Product 1

HCID 10220070HCID 10220070, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 18.0 g of (E)-3-(3-fluorophenyl)-2-butenoic acid in 200 ml of toluene was added 13.9 ml of triethylamine under cooling and a nitrogen atmosphere with stirring, followed by the addition of 13.0 ml of isobutyl chlorocarbonate, and then the solution was stirred at room temperature for 30 minutes. To the reaction solution cooled on ice was added dropwise 7.6 ml of cyclopropylamine with stirring, and the mixture was stirred at room temperature for 2 hours. Then, following a procedure similar to that of Example 6 to give 14.0 g of (E)-N-cyclopropyl-3-(3-fluorophenyl)-2-butenamide.

Workup

  1. temperatureunder cooling
  2. stirringthe solution was stirred at room temperature for 30 minutes
  3. temperatureTo the reaction solution cooled on ice
  4. stirringwith stirring
  5. stirringthe mixture was stirred at room temperature for 2 hours

Sources & evidence

ORD record
ord-04b7adcf83564cf4b3aeb2deca06370d
Source dataset
uspto-grants-1992_05
Patent number
US05116877

Reaction notes

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