Tetrafluoroborate → 1-(1-Benzyl-2-pyrrolidylidene)-3-(3-chloro-4-fluorophenyl)urea

HRID 1973938Notes

Reaction equation

HRID 1973938 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.[Cl:19][C:20]1[CH:21]=[C:22]([N:27]=[C:28]=[O:29])[CH:23]=[CH:24][C:25]=1[F:26]>>[CH2:6]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[N:18][C:28]([NH:27][C:22]1[CH:23]=[CH:24][C:25]([F:26])=[C:20]([Cl:19])[CH:21]=1)=[O:29])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 26255TetrafluoroborateHCID 27346323-Chloro-4-fluorophenyl isocyanateHCID 124490231-Benzyl-2-iminopyrrolidine

Product 1

HCID 541262321-(1-Benzyl-2-pyrrolidylidene)-3-(3-chloro-4-fluorophenyl)urea

Procedure

The fluoroborate salt of 1-benzyl-2-iminopyrrolidine (6.55 g.; 0.025 mole) is converted to the 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 4.29 g. (0.025 mole) of 3-chloro-4-fluorophenyl-isocyanate is added. The reaction mixture is stirred at room temperature for 1 hour and then evaporated to dryness in vacuo to give a solid residue. Recrystallizations from acetone-ether yields the pure product, 1-(1-benzyl-2-pyrrolidylidene)- 3-(3-chloro-4-fluorophenyl)urea, m.p. = 131°-132° C.

Workup

  1. dry with materialAfter drying over K2CO3
  2. filtrationthe benzene solution is filtered through diatomaceous earth and 4.29 g
  3. customevaporated to dryness in vacuo
  4. customto give a solid residue
  5. customRecrystallizations from acetone-ether

Sources & evidence

ORD record
ord-62a7ac44359c4251a97e6fef1aa5e233
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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