Ammonia → 4-(Chloromethyl)benzamide

HRID 2308078Notes

Reaction equation

HRID 2308078 reaction equation
[NH3:1].[Cl:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1>C1(C)C=CC=CC=1>[Cl:2][CH2:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:1])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 701364-(Chloromethyl)benzoyl chloride

Product 1

HCID 4583634-(Chloromethyl)benzamideYield 99.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 28% aqueous ammonia (19.3 g, 317 mmol, 4.0 eq) and toluene (30 mL) was dropwise added a 4-chloromethylbenzoyl chloride (15.0 g, 79.3 mmol)/toluene (30 mL) solution under ice-cooling. The mixture was stirred at room temperature for 1 hr. and under ice-cooling for 1 hr. The crystals were collected by filtration, washed with water (9 mL) and toluene (9 mL), and dried in vacuo at 40° C. to give the title compound (13.36 g, yield 99.3%) as white crystals.

Workup

  1. temperaturecooling
  2. temperatureand under ice-cooling for 1 hr
  3. filtrationThe crystals were collected by filtration
  4. washwashed with water (9 mL) and toluene (9 mL)
  5. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-32cfb4b5f97d47e4bbe3e6431908fb24
Source dataset
uspto-grants-2004_12
Patent number
US06833457B1

Reaction notes

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