Diethyl Ether → 2-chloro-N-(2-chloro-4-nitrophenyl)acetamide

HRID 1385224Notes

Reaction equation

HRID 1385224 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Cl:12][CH2:13][C:14](Cl)=[O:15].CCOCC>O1CCCC1>[Cl:12][CH2:13][C:14]([NH:4][C:3]1[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:2]=1[Cl:1])=[O:15]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6577Chloroacetyl chlorideHCID 84922-Chloro-4-nitroaniline

Product 1

HCID 37336412-chloro-N-(2-chloro-4-nitrophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-chloro-4-nitroaniline (19.0 g) and chloroacetyl chloride (30 mL) in tetrahydrofuran (150 mL) is heated at reflux for 1 hour. The solution is cooled and concentrated under reduced pressure, giving a wet yellow solid. Ether (250 mL) is added and the yellow solid is collected.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe solution is cooled
  3. concentrationconcentrated under reduced pressure
  4. customgiving a wet yellow solid
  5. customthe yellow solid is collected

Sources & evidence

ORD record
ord-cbadba10ded941f88d524f5e2e2db143
Source dataset
uspto-grants-2001_07
Patent number
US06262090B1

Reaction notes

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