Phosgene → 74738-34-4

HRID 1702605Notes

Reaction equation

HRID 1702605 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].[C:10](Cl)(Cl)=[O:11]>C(OC(=O)C)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([N:7]=[C:10]=[O:11])[CH:8]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 27348055-Bromo-o-toluidine

Product 1

HCID 2052605174738-34-4Yield 90.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 16.5 grams of 5-bromo-2-methyl aniline and 100 ml. of ethylacetate was added with stirring to a solution of 20 grams of phosgene and 300 ml. of ethylacetate kept at 5° C. After the addition was completed, phosgene was bubbled through the mixture while refluxing for one-half hour. The reaction mixture was purged with nitrogen, then the solvent was removed in vacuo to obtain 17 grams of 5-bromo-2-methylphenylisocyanate. This material was dissolved in 150 ml. of chloroform and added cautiously to a solution of 18.2 grams of 3-chloropropylamine hydrochloride, 150 ml. of chloroform, and 20 ml. of triethylamine. The mixture was refluxed for one-half hour, then cooled and shaken with water. The precipitated solid was separated by filtration. Recrystallization from ethylacetate afforded N-[3-(chloropropylamino)propyl]-N'-(5-bromo-2-methylphenyl)urea, m.p. 145°-148° C.

Workup

  1. customkept at 5° C
  2. additionAfter the addition
  3. customphosgene was bubbled through the mixture
  4. temperaturewhile refluxing for one-half hour
  5. customThe reaction mixture was purged with nitrogen
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d22b2cbb4fe94316b6b8557fd2e91545
Source dataset
uspto-grants-1982_09
Patent number
US04348413

Reaction notes

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