4-Nitroaniline → 2,3-Dibromo-N-[(4-nitrophenyl)carbamoyl]propanamide

HRID 259165Notes

Reaction equation

HRID 259165 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:11][CH:12]([CH2:18][Br:19])[C:13]([N:15]=[C:16]=[O:17])=[O:14]>C(#N)C>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:16]([NH:15][C:13](=[O:14])[CH:12]([Br:11])[CH2:18][Br:19])=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 74754-NitroanilineHCID 203185382,3-Dibromopropanoyl isocyanate

Product 1

HCID 214232842,3-Dibromo-N-[(4-nitrophenyl)carbamoyl]propanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

14.0 g of 4-nitroaniline are dissolved in 200 ml of anhydrous acetonitrile, and 26.0 g of 2,3-dibromopropionyl isocyanate are added dropwise with cooling at 5° to 10° C. After stirring for 3 hours at 20° C., the solid precipitated is filtered off and dried. Yield: 35.0 g m.p.: 205° - 206° C. (decomp.).

Workup

  1. temperaturewith cooling at 5° to 10° C
  2. customthe solid precipitated
  3. filtrationis filtered off
  4. customdried

Sources & evidence

ORD record
ord-748fbac827a44e89b2907f8c75a45eae
Source dataset
uspto-grants-1977_07
Patent number
US04036850

Reaction notes

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