Hydrochloric Acid → 4-Chloro-N-(2-hydroxyethyl)benzamide

HRID 2255113Notes

Reaction equation

HRID 2255113 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([CH2:13][NH2:14])[OH:12].C(N(CC)CC)C.Cl>C(Cl)Cl>[OH:12][CH2:11][CH2:13][NH:14][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 8471TriethylamineHCID 85014-Chlorobenzoyl chloride

Product 1

HCID 2339794-Chloro-N-(2-hydroxyethyl)benzamideYield 77.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.6 ml (0.02 mol) of 4-chlorobenzoyl chloride are added dropwise at 0° to a solution of 1.2 ml (0.02 mol) of ethanolamine and 3 ml (about 0.02 mol) of triethylamine in 30 ml of methylene chloride. The mixture is then poured into dilute hydrochloric acid and extracted twice with methylene chloride. The methylene chloride extracts are dried over magnesium sulfate and concentrated. After purification on silica gel using chloroform and chloroform/methanol 9:1) as the eluting agent, there are obtained 3.1 g of N-(2-hydroxyethyl)-4-chlorobenzamide.

Workup

  1. extractionextracted twice with methylene chloride
  2. dry with materialThe methylene chloride extracts are dried over magnesium sulfate
  3. concentrationconcentrated
  4. customAfter purification on silica gel

Sources & evidence

ORD record
ord-7dbe95ea779e4c689c1d27dc938a8b5b
Source dataset
uspto-grants-1993_08
Patent number
US05238962

Reaction notes

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