2,4,6-Trimethylphenyl isocyanate → 1-Mesityl-3-(1-methyl-2-pyrrolidylidene)urea

HRID 1973945Notes

Reaction equation

HRID 1973945 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[N:17]=[C:18]=[O:19]>C1C=CC=CC=1>[C:9]1([CH3:8])[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[NH:17][C:18]([N:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7])=[O:19]

Participants

4

Reactant 2

HCID 5952392,4,6-Trimethylphenyl isocyanateHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 545214411-Mesityl-3-(1-methyl-2-pyrrolidylidene)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The hydrochloride salt of 2-imino-1-methylpyrrolidine (6.73 g.; 0.05 mole) is converted to free base (4.0 g.; 0.05 mole) by adding 10 ml. of 50% NaOH to an aqueous slurry (minimal amount of water) of the salt and benzene extraction. After drying over K2CO3, the benzene solution is stirred at room temperature and 8.06 g. (0.05 mole) of 2,4,6-trimethylphenylisocyanate [made according to the method of K. Inukai and Y. Maki, Kogyo Kagaku Zasshi, 70 (4), 491-4 (1967)] dissolved in anhydrous benzene is added. The reaction mixture is stirred at room temperature for 11/2 hours and then the solvent is evaporated in vacuo leaving an oily residue, which crystallizes on cooling. Recrystallization from acetone yields the pure product, 1-mesityl-3-(1-methyl-2-pyrrolidylidene)urea, m.p. = 121°-123° C.

Workup

  1. additionby adding 10 ml
  2. extractionof 50% NaOH to an aqueous slurry (minimal amount of water) of the salt and benzene extraction
  3. dry with materialAfter drying over K2CO3
  4. additionis added
  5. stirringThe reaction mixture is stirred at room temperature for 11/2 hours
  6. customthe solvent is evaporated in vacuo
  7. customleaving an oily residue, which
  8. customcrystallizes
  9. temperatureon cooling
  10. customRecrystallization from acetone

Sources & evidence

ORD record
ord-50fc1ab1fd9c4bd4b4d0debe29da142a
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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