Carbamic chloride, N-methyl-N-phenyl- → 1-Methyl-3-(1-methyl-2-pyrrolidylidene)-1-phenylurea

HRID 1973929Notes

Reaction equation

HRID 1973929 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[CH3:8][N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10](Cl)=[O:11]>C1C=CC=CC=1>[CH3:8][N:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([N:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7])=[O:11]

Participants

4

Reactant 2

HCID 77969Carbamic chloride, N-methyl-N-phenyl-HCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 536696191-Methyl-3-(1-methyl-2-pyrrolidylidene)-1-phenylurea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The hydrochloride salt of 2-imino-1-methylpyrrolidine (13.46 g.; 0.1 mole) is converted to free base by adding 10 ml. of 50% NaOH and extracting into benzene. After drying over K2CO3, the benzene layer is stirred at room temperature and 8.48 g. (0.05 mole) of N-methyl-phenylcarbamoyl chloride (prepared according to the method of J. A. Aeschlimann, U.S. Pat. No. 2,449,440), dissolved in anhydrous benzene, is added dropwise to this solution. Cloudiness occurs and then solid precipitates from solution. The mixture is stirred at room temperature overnight and then filtered. The filtrate is taken to dryness in vacuo to an oily residue which is dissolved in hot hexane and filtered hot. Cooling and scratching yields crystals which are collected and recrystallized from hexane to give the pure product, 1-methyl-3-(1-methyl-2-pyrrolidylidene)-1-phenylurea, 27.5°-30° C.

Workup

  1. additionby adding 10 ml
  2. extractionof 50% NaOH and extracting into benzene
  3. dry with materialAfter drying over K2CO3
  4. additionis added dropwise to this solution
  5. customsolid precipitates from solution
  6. stirringThe mixture is stirred at room temperature overnight
  7. filtrationfiltered
  8. dissolutionis dissolved in hot hexane
  9. filtrationfiltered hot
  10. temperatureCooling
  11. customscratching yields crystals which
  12. customare collected
  13. customrecrystallized from hexane

Sources & evidence

ORD record
ord-e5632d4b5fba4fda9cc7a2f827afd046
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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