Ethanolamine → HCID 9497550, compound

HRID 2260710Notes

Reaction equation

HRID 2260710 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[NH2:13][CH2:14][CH2:15][OH:16].[OH-].[Na+]>Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([NH:13][CH2:14][CH2:15][OH:16])=[O:8]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 123841765-Chloro-2-methoxybenzoyl chloride

Product 1

HCID 9497550HCID 9497550, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5-Chloro-2-methoxybenzoyl chloride (5.0 g) was added to a vigorously stirred mixture of 2-aminoethanol (10.12 g, 10 ml) and sodium hydroxide solution (1M, 100 ml). Stirring was continued for 2 hours at room temperature, then dilute hydrochloric acid (10% v/v, 100 ml) was added and the mixture extracted with dichloromethane (3×200 ml). The combined dichloromethane layers were dried (MgSO4) and evaporated, and the resulting oil chromatographed on silica gel with 1% methanol in dichloromethane as solvent to afford the title compound as an oil.

Workup

  1. extractionthe mixture extracted with dichloromethane (3×200 ml)
  2. dry with materialThe combined dichloromethane layers were dried (MgSO4)
  3. customevaporated
  4. customthe resulting oil chromatographed on silica gel with 1% methanol in dichloromethane as solvent

Sources & evidence

ORD record
ord-11aa0096331442639b8edee63b764339
Source dataset
uspto-grants-1995_12
Patent number
US05478851

Reaction notes

Loading…