Ammonium Hydroxide → 3-Chloromethyl-benzamide

HRID 1729194Notes

Reaction equation

HRID 1729194 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[NH4+:12].[OH-]>C(Cl)Cl>[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH2:12])=[O:7]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 27333243-(Chloromethyl)benzoyl chloride

Product 1

HCID 7371453-Chloromethyl-benzamideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 66.50 g (0.352 mol, 1.0 mol-equiv) 3-chloromethylbenzoylchloride in 400 mL CH2Cl2 at 0°-5° C. under argon was added 47.6 mL (0.704, 2.0 mol-equiv) concentrated aqueous NH4OH over 25 min. The resulting slurry was filtered, washed with water and the product was dried overnight at 50° C. under vacuum to provide 48.59 g (81%) of 3-chloromethylbenzamide.

Workup

  1. filtrationThe resulting slurry was filtered
  2. washwashed with water
  3. customthe product was dried overnight at 50° C. under vacuum

Sources & evidence

ORD record
ord-b089139e4ae8413fbcd2807f83d62c56
Source dataset
uspto-grants-1994_07
Patent number
US05332738

Reaction notes

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