m-Tolyl isocyanate → 1-(1-Methylpyrrolidin-2-ylidene)-3-(m-tolyl)urea

HRID 1973932Notes

Reaction equation

HRID 1973932 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[C:8]1([CH3:17])[CH:13]=[CH:12][CH:11]=[C:10]([N:14]=[C:15]=[O:16])[CH:9]=1>>[CH3:17][C:8]1[CH:9]=[C:10]([NH:14][C:15]([N:1]=[C:2]2[CH2:6][CH2:5][CH2:4][N:3]2[CH3:7])=[O:16])[CH:11]=[CH:12][CH:13]=1

Participants

3

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 30393611-(1-Methylpyrrolidin-2-ylidene)-3-(m-tolyl)urea

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, and 6.66 g. (0.05 mole) of m-tolylisocyanate is added (solid forms). The reaction mixture is stirred at room temperature overnight. The solid is collected, m.p. = 148°-149° C. The benzene filtrate, after removal of solvent, yields a further crop of solid material, m.p. 137°-142° C. Recrystallizations of the combined solids from acetone gives the pure product, 1-m-methylphenyl-3-(1-methyl-2-pyrrolidylidene)urea, m.p. = 149°-151° C.

Workup

  1. dry with materialAfter drying over K2CO3
  2. stirringThe reaction mixture is stirred at room temperature overnight
  3. customThe solid is collected
  4. customThe benzene filtrate, after removal of solvent
  5. customyields a further crop of solid material, m.p. 137°-142° C
  6. customRecrystallizations of the combined solids from acetone

Sources & evidence

ORD record
ord-08658c18254e40b5a0e3b15adee40b9f
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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