Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 5-{3-[(2-Chloroethyl)oxy]phenyl}-2-thiophenecarboxamide

HRID 70260

Reaction equation

HRID 70260 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C1(C)C=CC(S(O[CH2:26][CH2:27][Cl:28])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:28][CH2:27][CH2:26][O:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([NH2:15])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 11430Potassium CarbonateHCID 671598185-(3-Hydroxyphenyl)-2-thiophenecarboxamide

Product 1

HCID 582762485-{3-[(2-Chloroethyl)oxy]phenyl}-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(3-Hydroxyphenyl)-2-thiophenecarboxamide (0.31 g, 1.41 mmol), 2-chloroethyl p-toluenesulfonate (1.327 g, 5.65 mmol) and potassium carbonate (0.782 g, 5.65 mmol) in 20 ml of acetonitrile were heated to reflux for 15 h. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (50 to 80% ethyl acetate in hexanes) to give the title compound as a white solid.

Workup

  1. temperatureto reflux for 15 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. custompurified by silica gel column chromatography (50 to 80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c81fcc60d7d54774b3aa20fb85f374c1
Source dataset
uspto-grants-2014_09
Patent number
US08822518B2

Linked notes

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