Benzene, 1-chloro-3-isocyanato- → HCID 3039369, compound

HRID 1973946Notes

Reaction equation

HRID 1973946 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[NH:8])[CH3:2].[Cl:9][C:10]1[CH:11]=[C:12]([N:16]=[C:17]=[O:18])[CH:13]=[CH:14][CH:15]=1>C1C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([N:8]=[C:4]2[CH2:5][CH2:6][CH2:7][N:3]2[CH2:1][CH3:2])=[O:18])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 12449021HCID 12449021, compound

Product 1

HCID 3039369HCID 3039369, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The hydrochloride salt of 1-ethyl-2-iminopyrrolidine (7.43 g.; 0.05 mole) is converted to free base (5.6 g.; 0.05 mole) by adding 7 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 7.68 g. (0.05 mole) of m-chlorophenylisocyanate, dissolved in anhydrous benzene, is added. The reaction mixture is stirred for 13/4 hours and the solvent is then evaporated in vacuo leaving a solid residue, 1-m-chlorophenyl-3-(1-ethyl-2-pyrrolidylidene)urea. Recrystallizations from ethyl acetate yields the pure product, m.p. = 122°-124° C.

Workup

  1. additionby adding 7 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 for 13/4 hours
  6. customthe solvent is then evaporated in vacuo

Sources & evidence

ORD record
ord-ce93a36bce9640f48f64993b66bf5c11
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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