Water → 5-[4-(2-Isopropyl-phenoxy)-benzylidene]-2-methylsulfanyl-thiazol-4-one

HRID 2040112Notes

Reaction equation

HRID 2040112 reaction equation
[CH:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][C:7]1[CH:20]=[CH:19][C:10]([CH:11]=[C:12]2[S:16][C:15](=[S:17])[NH:14][C:13]2=[O:18])=[CH:9][CH:8]=1)([CH3:3])[CH3:2].CI.[CH:27](N(C(C)C)CC)(C)C.O>C(O)C>[CH:1]([C:4]1[CH:24]=[CH:23][CH:22]=[CH:21][C:5]=1[O:6][C:7]1[CH:20]=[CH:19][C:10]([CH:11]=[C:12]2[S:16][C:15]([S:17][CH3:27])=[N:14][C:13]2=[O:18])=[CH:9][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 866231455-[4-(2-Isopropyl-phenoxy)-benzylidene]-2-thioxo-thiazolidin-4-one

Product 1

HCID 690899295-[4-(2-Isopropyl-phenoxy)-benzylidene]-2-methylsulfanyl-thiazol-4-oneYield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-[4-(2-Isopropyl-phenoxy)-benzylidene]-2-thioxo-thiazolidin-4-one (0.4 g, 1.12 mmol) in Ethanol (14 mL) was added CH3I (0.32 g, 2.25 mmol) and diisopropylethylamine (0.17 g, 1.35 mmol). The reaction mixture was stirred at room temperature for 4 h. It was then added water (40 mL) and the slurry was stirred at room temperature for 30 minutes. The solid was filtered, washed with water to yield the 5-[4-(2-Isopropyl-phenoxy)-benzylidene]-2-methylsulfanyl-thiazol-4-one as a yellow solid (0.42 g, 94%)

Workup

  1. filtrationThe solid was filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-e1e78565f58b45a1a50e2094fbf2e5bf
Source dataset
uspto-grants-2013_11
Patent number
US08580832B2

Reaction notes

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