Hydrochloric Acid → N-(2,6-Dimethylphenyl)-N′-(1-ethyl-2-pyrrolidinylidene)urea

HRID 1973947Notes

Reaction equation

HRID 1973947 reaction equation
Cl.[CH2:2]([N:4]1[CH2:8][CH2:7][CH2:6][C:5]1=[NH:9])[CH3:3].[CH3:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:12]=1[N:18]=[C:19]=[O:20].C(OCC)(=O)C>C1C=CC=CC=1>[CH3:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH3:10])[C:12]=1[NH:18][C:19]([N:9]=[C:5]1[CH2:6][CH2:7][CH2:8][N:4]1[CH2:2][CH3:3])=[O:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 987872,6-Xylyl isocyanateHCID 12449021HCID 12449021, compound

Product 1

HCID 54210342N-(2,6-Dimethylphenyl)-N′-(1-ethyl-2-pyrrolidinylidene)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The hydrochloride of 1-ethyl-2-iminopyrrolidine (7.43 g.; 0.05 mole) is converted to free base (5.6 g.; 0.05 mole) in benzene in the usual manner. Then 7.35 g. (0.05 mole) of 2,6-dimethylphenylisocyanate, dissolved in anhydrous benzene, is added. The reaction mixture is stirred at room temperature for 13/4 hours and then the solvent is evaporated to dryness in vacuo to give an oily residue. Trituration with ethyl acetate and cooling produces a solid product, 1-(2,6-dimethylphenyl)-3-(1-ethyl-2-pyrrolidylidene)urea, m.p. = 120°-122° C. Recrystallization from acetone gives the pure product, m.p. - 121°-123° C.

Workup

  1. additionis added
  2. customthe solvent is evaporated to dryness in vacuo
  3. customto give an oily residue

Sources & evidence

ORD record
ord-caa475f50efb4e45912a5cba56e987bd
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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