3-(Trifluoromethyl)phenyl isocyanate → HCID 4226732, compound

HRID 482905Notes

Reaction equation

HRID 482905 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][NH2:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[F:10][C:11]([F:22])([F:21])[C:12]1[CH:13]=[C:14]([N:18]=[C:19]=[O:20])[CH:15]=[CH:16][CH:17]=1>C1(C)C=CC=CC=1>[N:1]1([CH2:6][CH2:7][CH2:8][NH:9][C:19]([NH:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:11]([F:10])([F:21])[F:22])[CH:13]=2)=[O:20])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 787361H-Imidazole-1-propanamine

Product 1

HCID 4226732HCID 4226732, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 2.50 g. portion of 1H-imidazole-1-propanamine was added to 20 ml. of toluene. A solution of 3.7 g. of m-trifluoromethylphenyl isocyanate in 20 ml. of toluene was added and the mixture was stirred overnight, then evaporated to a syrup. This syrup was triturated twice with ether giving 4.95 g. of crystals. These crystals were dissolved in methylene chloride, hot ethyl acetate or a mixture of the two and passed through a silica gel column, developing with 200 ml. of ethyl acetate and discarding the 200 ml. fraction. The column was then eluted with 10% methanol in ethyl acetate, collecting three 200 ml. fractions. These fractions were combined and evaporated in vacuo, giving 4.33 g. of the desired product as colorless waxy crystals, mp 105°-108° C.

Workup

  1. customevaporated to a syrup
  2. customThis syrup was triturated twice with ether giving 4.95 g
  3. dissolutionThese crystals were dissolved in methylene chloride
  4. additionhot ethyl acetate or a mixture of the two
  5. washThe column was then eluted with 10% methanol in ethyl acetate
  6. customcollecting three 200 ml
  7. customevaporated in vacuo
  8. customgiving 4.33 g

Sources & evidence

ORD record
ord-511ff4cdb36b464fa5aa46bfed760e2a
Source dataset
uspto-grants-1986_03
Patent number
US04576957

Reaction notes

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