Acetonitrile → 4-(3-Chloropropoxy)benzamide

HRID 1183797Notes

Reaction equation

HRID 1183797 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C.Br[CH2:21][CH2:22][CH2:23][Cl:24]>O>[Cl:24][CH2:23][CH2:22][CH2:21][O:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 650524-Hydroxybenzamide

Product 1

HCID 144071764-(3-Chloropropoxy)benzamideYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

10.5 kg of 4-hydroxybenzamide, 10.58 kg of potassium carbonate and 83 kg of acetonitrile are introduced into a reactor. The mixture is stirred and then there are added 24.14 kg of a solution of 1-bromo-3-chloropropane. The reaction mixture is heated at reflux for 4 hours. Water (105 L) is added in the hot state, the mixture is then cooled to 5° C. and filtered. The filter cake is washed with water and then with acetonitrile. The title product is obtained in the form of a powder in a yield of 82%.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. washThe filter cake is washed with water

Sources & evidence

ORD record
ord-f608d590417449338b580aa4d03108a0
Source dataset
uspto-grants-2014_03
Patent number
US08664408B2

Reaction notes

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