Chloroacetyl chloride → Acetanilide, 2-chloro-4'-nitro-

HRID 1451648Notes

Reaction equation

HRID 1451648 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].C(=O)([O-])[O-].[K+].[K+].[N+:12]([C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1)([O-:14])=[O:13]>CN(C=O)C>[Cl:1][CH2:2][C:3]([NH:19][C:18]1[CH:20]=[CH:21][C:15]([N+:12]([O-:14])=[O:13])=[CH:16][CH:17]=1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 74754-NitroanilineHCID 11430Potassium Carbonate

Product 1

HCID 140220Acetanilide, 2-chloro-4'-nitro-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloroacetyl chloride (11 ml) was added dropwise to a stirred mixture of potassium carbonate (18.8 g) and 4-nitroaniline (15 g) in DMF (100 ml) maintained at 0°. The mixture was then allowed to stand overnight at room temperature and poured into crushed ice. A yellow solid was recovered and crystallised from toluene containing isopropyl alcohol (10%) to give the title compound (10 g), MP: 180°.

Workup

  1. temperaturemaintained at 0°
  2. additionpoured
  3. custominto crushed ice
  4. customA yellow solid was recovered
  5. customcrystallised from toluene
  6. additioncontaining isopropyl alcohol (10%)

Sources & evidence

ORD record
ord-c91fde5a3e334306866df296a298edab
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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