Ethanol → N-(2,6-diisopropylphenyl)-2-(6-chlorohexylthio)acetamide

HRID 36761Notes

Reaction equation

HRID 36761 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:20])[CH2:15][S:16][C:17](=O)[CH3:18])([CH3:3])[CH3:2].C(O)C.[OH-].[Na+].BrCC[CH2:29][CH2:30][CH2:31][CH2:32][Cl:33]>O>[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([CH3:12])[CH3:11])[C:5]=1[NH:13][C:14](=[O:20])[CH2:15][S:16][CH2:17][CH2:18][CH2:29][CH2:30][CH2:31][CH2:32][Cl:33])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 805161-Bromo-6-chlorohexaneHCID 15289526HCID 15289526, compound

Product 1

HCID 15289527N-(2,6-diisopropylphenyl)-2-(6-chlorohexylthio)acetamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 29.3 g of N-(2,6-diisopropylphenyl)-2-(acetylthio)acetamide and 240 ml of ethanol was added dropwise 27 ml of a 30% aqueous sodium hydroxide solution at 0° C. in an argon atmosphere. After stirring for 30 minutes, 20.0 g of 1-bromo-6-chlorohexane was added thereto, followed by stirring at room temperature for 4 hours. To the reaction mixture was added 50 ml of water to yield 36.0 g of N-(2,6-diisopropylphenyl)-2-(6-chlorohexylthio)acetamide as colorless needle crystals having a melting point (m.p.) of 86.5° to 87.5° C.

Workup

  1. stirringby stirring at room temperature for 4 hours

Sources & evidence

ORD record
ord-5d167a2f4e0641dc9c62387357701330
Source dataset
uspto-grants-1995_05
Patent number
US05416212

Reaction notes

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