3-(Trifluoromethyl)phenyl isocyanate → HCID 54551796, compound

HRID 2071503Notes

Reaction equation

HRID 2071503 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[F:8][C:9]([F:20])([F:19])[C:10]1[CH:11]=[C:12]([N:16]=[C:17]=[O:18])[CH:13]=[CH:14][CH:15]=1>>[CH3:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[N:1][C:17]([NH:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:9]([F:8])([F:19])[F:20])[CH:11]=1)=[O:18]

Participants

3

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 54551796HCID 54551796, compound

Procedure

Conversion of the hydrochloride salt of 2-imino-1-methylpyrrolidine (6.73 g.; 0.05 mole) to the free base (4.9 g. assuming 100% conversion) is carried out in the usual manner. After drying over K2CO3 the benzene layer is stirred at room temperature and 9.36 g. (0.05 mole) of m-trifluoromethylphenylisocyanate is added (some solid precipitates). The reaction mixture is stirred overnight. The resulting solid is collected, m.p. = 155°-156° C. The benzene filtrate, upon removal of the solvent, affords an additional crop of solid material, m.p. 131°-137° C. Recrystallizations of the combined solids from acetone-pet. ether gives the pure product, 1-(1-methyl-2-pyrrolidylidene)-3-(m-trifluoromethylphenyl)urea, m.p. = 155°-156.5° C.

Workup

  1. dry with materialAfter drying over K2CO3 the benzene layer
  2. customprecipitates)
  3. stirringThe reaction mixture is stirred overnight
  4. customThe resulting solid is collected
  5. customThe benzene filtrate, upon removal of the solvent
  6. customaffords an additional crop of solid material, m.p. 131°-137° C
  7. customRecrystallizations of the combined solids from acetone-pet. ether

Sources & evidence

ORD record
ord-255a5024b4224cae9f4cede1fc89f1d1
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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