2,4,6-Tribromophenyl isocyanate → 1-(1-Methyl-2-pyrrolidylidene)-3-(2,4,6-tribromophenyl)urea

HRID 2071513Notes

Reaction equation

HRID 2071513 reaction equation
[NH:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH3:7].[Br:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[C:11]([Br:16])[C:10]=1[N:17]=[C:18]=[O:19]>C1C=CC=CC=1>[CH3:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[N:1][C:18]([NH:17][C:10]1[C:11]([Br:16])=[CH:12][C:13]([Br:15])=[CH:14][C:9]=1[Br:8])=[O:19]

Participants

4

Reactant 2

HCID 33866432,4,6-Tribromophenyl isocyanateHCID 124489661-Methyl-2-pyrrolidinimine

Product 1

HCID 538378321-(1-Methyl-2-pyrrolidylidene)-3-(2,4,6-tribromophenyl)urea

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The hydrochloride salt of 2-imino-1-methylpyrrolidine (6.73 g.; 0.05 mole) is converted to free base (4.0 g.; 0.05 mole - assuming 100% conversion) by adding 5 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 16.79 g. (0.0472 mole) of 2,4,6-tribromophenylisocyanate [made according to the method of K. Inukai and Y. Maki, Kogyo Kagaku Zasshi, 70 (4), 491-4 (1967)] dissolved in anhydrous benzene, is added with stirring. The reaction mixture is stirred for 2 hours and then the solvent is evaporated in vacuo to give a solid residue of 1-(1-methyl-2-pyrrolidylidene)-3-(2,4,6-tribromophenyl)urea. Recrystallizations from acetone yields the pure product, m.p. = 165°-167.5° C. EXAMPLE XXXVII

Workup

  1. additionby adding 5 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. stirringwith stirring
  6. stirringThe reaction mixture is stirred for 2 hours
  7. customthe solvent is evaporated in vacuo

Sources & evidence

ORD record
ord-397216c81c1c4e92a3862e958c6c1598
Source dataset
uspto-grants-1977_09
Patent number
US04046909

Reaction notes

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