Tetrafluoroboric acid → 1-(2,6-Dimethylphenyl)-3-(1,5-dimethyl-2-pyrrolidylidene)urea

HRID 2071520

Reaction equation

HRID 2071520 reaction equation
[H+].[B-](F)(F)(F)F.[CH3:7][N:8]1[CH:12]([CH3:13])[CH2:11][CH2:10][C:9]1=[NH:14].[CH3:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[C:17]=1[N:23]=[C:24]=[O:25]>C1C=CC=CC=1>[CH3:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH3:15])[C:17]=1[NH:23][C:24]([N:14]=[C:9]1[CH2:10][CH2:11][CH:12]([CH3:13])[N:8]1[CH3:7])=[O:25]

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 987872,6-Xylyl isocyanateHCID 124490241,5-Dimethyl-2-iminopyrrolidine

Product 1

HCID 545552241-(2,6-Dimethylphenyl)-3-(1,5-dimethyl-2-pyrrolidylidene)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The HBF4 salt of 1,5-dimethyl-2-iminopyrrolidine (6.75 g.; 0.0337 mole) is converted to free base in benzene in the usual manner. Then 4.96 g. (0.0337 mole) of 2,6-dimethylphenylisocyanate, dissolved in anhydrous benzene, is added. The reaction mixture is stirred for 2 hours and then the solvent is evaporated in vacuo leaving a oily residue which eventually crystallizes. Recrystallization from ethyl acetate gives the product, 1-(2,6-dimethylphenyl)-3-(1,5-dimethyl-2-pyrrolidylidene)urea, m.p. 120°-122° C.

Workup

  1. additionis added
  2. customthe solvent is evaporated in vacuo
  3. customleaving a oily residue which
  4. customeventually crystallizes
  5. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-abda39b20b4041b48b4701e511709de0
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Linked notes

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