4-Isocyanato-1,2-dimethoxybenzene → N-(3,4-Dimethoxyphenyl)-N'-(1-methylpyrrolidin-2-ylidene)urea

HRID 2071489Notes

Reaction equation

HRID 2071489 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([N:18]=[C:19]=[O:20])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]>C1C=CC=CC=1>[CH3:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[N:1][C:19]([NH:18][C:12]1[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:10]([O:9][CH3:8])[CH:11]=1)=[O:20]

Participants

4

Reactant 2

HCID 35178104-Isocyanato-1,2-dimethoxybenzeneHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 54339111N-(3,4-Dimethoxyphenyl)-N'-(1-methylpyrrolidin-2-ylidene)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

After dissolving 5.4 g. (0.055 mole) of 2-imino-1-methylpyrrolidine in dry benzene, 9.85 g. (0.055 mole) of 3,4-dimethoxyphenylisocyanate (prepared according to the method of J. G. Lombardino and C. T. Gerber, J. Med. Chem., 7, Jan. 1964, p. 101), dissolved in dry benzene, is added dropwise to the solution. The reaction mixture is stirred at room temperature overnight (about 16 hrs.). The solvent is evaporated in vacuo and the residue, which solidifies on cooling, is triturated with anhydrous methanol. Repeated recrystallization from methanol yields the pure product, 1-(1-methyl-2-pyrrolidylidene)-3-(3,4-dimethoxyphenyl)urea, m.p. = 118°-120° C.

Workup

  1. dissolutionAfter dissolving 5.4 g
  2. additionis added dropwise to the solution
  3. customThe solvent is evaporated in vacuo
  4. temperatureon cooling
  5. customis triturated with anhydrous methanol
  6. customrecrystallization from methanol

Sources & evidence

ORD record
ord-c5efc32675df42fcb8c0bcc5bd641db4
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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