Benzene, 1-chloro-3-isocyanato- → 1-(1-Benzyl-2-pyrrolidylidene)-3-(m-chlorophenyl)urea

HRID 1973937Notes

Reaction equation

HRID 1973937 reaction equation
F[B-](F)(F)F.[CH2:6]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[NH:18])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:19][C:20]1[CH:21]=[C:22]([N:26]=[C:27]=[O:28])[CH:23]=[CH:24][CH:25]=1>C1C=CC=CC=1>[CH2:6]([N:13]1[CH2:17][CH2:16][CH2:15][C:14]1=[N:18][C:27]([NH:26][C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([Cl:19])[CH:21]=1)=[O:28])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 17968Benzene, 1-chloro-3-isocyanato-HCID 26255TetrafluoroborateHCID 124490231-Benzyl-2-iminopyrrolidine

Product 1

HCID 539311011-(1-Benzyl-2-pyrrolidylidene)-3-(m-chlorophenyl)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The fluoroborate salt of 1-benzyl-2-iminopyrrolidine (6.55 g.; 0.025 mole) is converted to free base (4.36 g.; 0.025 mole -- assuming 100% conversion) by adding 5 ml. of 50% NaOH to an aqueous slurry of the salt and benzene extraction. After drying over K2CO3, the benzene solution is filtered through diatomaceous earth and 3.84 g. (0.025 mole) of m-chlorophenylisocyanate, dissolved in anhydrous benzene, is added. The reaction mixture is stirred at room temperature for 2 hours and then taken to dryness in vacuo to give an oily residue which eventually crystallizes. Recrystallizations from acetonepetroleum ether affords a pure product, 1-(1-benzyl-2 -pyrrolidylidene)-3-(m-chlorophenyl)urea, m.p. = 91°-93° C.

Workup

  1. additionby adding 5 ml
  2. extractionof 50% NaOH to an aqueous slurry of the salt and benzene extraction
  3. dry with materialAfter drying over K2CO3
  4. filtrationthe benzene solution is filtered through diatomaceous earth and 3.84 g
  5. additionis added
  6. customto give an oily residue which
  7. customeventually crystallizes
  8. customRecrystallizations from acetonepetroleum ether

Sources & evidence

ORD record
ord-229a79641aac4015a1899fc2326692ee
Source dataset
uspto-grants-1976_12
Patent number
US03998958

Reaction notes

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