Methoxyacetyl chloride → 3,5-Bis(methoxyacetylamino)-4-chlorobenzonitrile

HRID 1165880Notes

Reaction equation

HRID 1165880 reaction equation
[Cl:1][C:2]1[C:9]([NH2:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[NH2:11].[CH3:12][O:13][CH2:14][C:15](Cl)=[O:16]>N1C=CC=CC=1>[CH3:12][O:13][CH2:14][C:15]([NH:11][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([NH:10][C:15](=[O:16])[CH2:14][O:13][CH3:12])[C:2]=1[Cl:1])[C:6]#[N:7])=[O:16]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chlorideHCID 124029953,5-Diamino-4-chlorobenzonitrile

Product 1

HCID 146992833,5-Bis(methoxyacetylamino)-4-chlorobenzonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-chloro-3,5-diaminobenzonitrile (3.34 g) in pyridine (60 ml) is added dropwise methoxyacetyl chloride (4.0 ml) at room temperature. The mixture is stirred at room temperature for 2 hours, and thereafter, pyridine is distilled off under reduced pressure. To the residue is added water, and the resulting solid substance is separated by filtration and washed with water. The resulting crude crystals are recrystallized from ethanol to give the title compound (5.1 g) having the following physical properties.

Workup

  1. distillationpyridine is distilled off under reduced pressure
  2. additionTo the residue is added water
  3. customthe resulting solid substance is separated by filtration
  4. washwashed with water
  5. customThe resulting crude crystals are recrystallized from ethanol

Sources & evidence

ORD record
ord-012e51196b8f4431b52d32b3bb8cf243
Source dataset
uspto-grants-1990_03
Patent number
US04912135

Reaction notes

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