3-(Trifluoromethyl)phenyl isocyanate → 1-(1-Benzyl-2-pyrrolidylidene)-3-(m-trifluoromethylphenyl)urea

HRID 2071510Notes

Reaction equation

HRID 2071510 reaction equation
F[B-](F)(F)F.[CH2:6]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[NH:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[F:19][C:20]([F:31])([F:30])[C:21]1[CH:22]=[C:23]([N:27]=[C:28]=[O:29])[CH:24]=[CH:25][CH:26]=1>>[CH2:6]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[N:18][C:28]([NH:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([F:19])([F:30])[F:31])[CH:22]=1)=[O:29])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 26255TetrafluoroborateHCID 124490231-Benzyl-2-iminopyrrolidine

Product 1

HCID 543452221-(1-Benzyl-2-pyrrolidylidene)-3-(m-trifluoromethylphenyl)urea

Procedure

The fluoroborate salt of 1-benzyl-2-iminopyrrolidine (6.55 g.; 0.025 mole) is converted to free base (4.36 g; 0.025 mole) in the usual manner. After drying over K2CO3, the benzene solution is filtered through diatomaceous earth and 4.68 g. (0.025 mole) of m-trifluoromethylphenylisocyanate is added. The reaction mixture is stirred at room temperature for 1 hour and then evaporated to dryness in vacuo to give an oily residue of 1-(1-benzyl-2-pyrrolidylidene)-3-(m-trifluoromethylphenyl)urea which is dissolved in ether and converted to the hydrochloride salt. Recrystallizations from acetone-ether yields the pure product, 1-(1-benzyl-2-pyrrolidylidene)-3-(m-trifluoromethylphenyl)urea HCl, m.p. = 164°-165° C.

Workup

  1. dry with materialAfter drying over K2CO3
  2. filtrationthe benzene solution is filtered through diatomaceous earth and 4.68 g
  3. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4144107f883249b39c01b77792af62e8
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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