4-Chlorobenzoyl chloride → HCID 14097617, compound

HRID 1762178Notes

Reaction equation

HRID 1762178 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C(Cl)(Cl)Cl>[Cl:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH:1][CH2:2][CH2:3][O:4][C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)=[O:27])=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 85014-Chlorobenzoyl chlorideHCID 11430Potassium CarbonateHCID 14097616Methyl 4-(2-aminoethoxy)benzoate

Product 1

HCID 14097617HCID 14097617, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl 4-(2-aminoethoxy)benzoate (19.5 g) and 13.8 g of anhydrous potassium carbonate were added to 200 ml of chloroform and the mixture was stirred with cooling. p-Chlorobenzoyl chloride (17.5 g) was dropped thereinto at 10°-20° C. The mixture was stirred for 3 hours. The reaction solution was washed with water, the chloroform layer was dried with anhydrous magnesium sulphate, concentrated in vacuo, the residue was crystallised with n-hexane, and the crystals were recrystallised with ethyl acetate/n-hexane to give 25.4 g of crystals of m.p. 125°-127° C., yield 76%.

Workup

  1. temperaturewith cooling
  2. customat 10°-20° C
  3. stirringThe mixture was stirred for 3 hours
  4. washThe reaction solution was washed with water
  5. dry with materialthe chloroform layer was dried with anhydrous magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customthe residue was crystallised with n-hexane
  8. customthe crystals were recrystallised with ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-80635c4d608844aca96250ff5798e3ee
Source dataset
uspto-grants-1989_05
Patent number
US04831055

Reaction notes

Loading…