4-Chlorophenol → alpha-Hydroxy-beta-(4-Chlorophenoxy)-N-(1-Methylethyl)-4-Chlorobenzenepropanamide

HRID 435504

Reaction equation

HRID 435504 reaction equation
[CH3:1][CH:2]([NH:4][C:5]([CH:7]1[CH:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[O:8]1)=[O:6])[CH3:3].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.[H-].[Na+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[OH:8][CH:7]([CH:9]([O:24][C:21]1[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=1)[C:10]1[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=1)[C:5]([NH:4][CH:2]([CH3:1])[CH3:3])=[O:6]

Participants

6

Reactant 4

HCID 46844-ChlorophenolHCID 24758Sodium hydrideHCID 2855718-Crown-6HCID 13041336N-(1-methylethyl)-3-(4-chlorophenyl)-2-oxiranecarboxamide

Product 1

HCID 13041348alpha-Hydroxy-beta-(4-Chlorophenoxy)-N-(1-Methylethyl)-4-Chlorobenzenepropanamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was prepared from N-(1-methylethyl)-3-(4-chlorophenyl)-2-oxiranecarboxamide (9.56 g.), p-chlorophenol (5.2 g.), sodium hydride (50% oil dispersion, 2.0 g.) 18-crown-6 (3.0 g.), and acetonitrile (300 ml.) as described in Example 12, and purified by recrystallization from ether. The compound melted at 177°-179°, and weighed 0.76 g.

Workup

  1. custompurified by recrystallization from ether

Sources & evidence

ORD record
ord-8ff4bd9544a14d28bffc2941761c3c75
Source dataset
uspto-grants-1983_08
Patent number
US04401832

Linked notes

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