Aniline → 2,3-Dibromo-N-(phenylcarbamoyl)propanamide

HRID 259163Notes

Reaction equation

HRID 259163 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][CH:9]([CH2:15][Br:16])[C:10]([N:12]=[C:13]=[O:14])=[O:11]>C1C=CC=CC=1>[C:2]1([NH:1][C:13]([NH:12][C:10](=[O:11])[CH:9]([Br:8])[CH2:15][Br:16])=[O:14])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 203185382,3-Dibromopropanoyl isocyanate

Product 1

HCID 203185402,3-Dibromo-N-(phenylcarbamoyl)propanamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
12.5 °C

Procedure

9.5 g of aniline are dissolved in 100 ml of anhydrous benzene and a solution of 26.0 g of 2,3-dibromopropionyl isocyanate in 100 ml of benzene is added dropwise with cooling at 10 to 15° C. After stirring for 2 hours, the crystal sludge is diluted with the same volume of petroleum ether, filtered, washed with petroleum ether and dried. Yield: 30.0 g, m.p: 160°-161° C.

Workup

  1. filtrationfiltered
  2. washwashed with petroleum ether
  3. customdried

Sources & evidence

ORD record
ord-280ea10ba53740659e5917008497853f
Source dataset
uspto-grants-1977_07
Patent number
US04036850

Reaction notes

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