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

HRID 1973934Notes

Reaction equation

HRID 1973934 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
  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-370c3c6b097b4f7a9dc735849b6dcec2
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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