Water → HCID 57056771, compound

HRID 2396819Notes

Reaction equation

HRID 2396819 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([C:16](=[C:18]2[S:22][C:21](=[S:23])[NH:20][C:19]2=[O:24])[CH3:17])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].IC.[CH:27](N(C(C)C)CC)(C)C.O>C(O)C>[CH3:15][C:12]([C:9]1[CH:8]=[C:7]([C:16](=[C:18]2[S:22][C:21]([S:23][CH3:27])=[N:20][C:19]2=[O:24])[CH3:17])[CH:6]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 54482101HCID 54482101, compound

Product 1

HCID 57056771HCID 57056771, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-[1-[3,5-bis(1,1-dimethylethyl)-4hydroxyphenyl]ethylidene]-2-thioxo-4-thiazolidinone (1.6 g, 4 mmoles), iodomethane (0.45 mL, 7 mmoles), and diisopropylethylamine (1.1 mL, 6 mmoles) in 20 mL of ethanol is stirred under N2 at room temperature for 16 hours, then stirred into 200 mL of water. The precipitate is filtered off, rinsed with water, and dried to afford the product (1.4 g) of 5-[1-[3,5bis(1,1-dimethylethyl)-4-hydroxyphenyl]-ethylidene]-2-(methylthio)-4(5H)-thiazolone, mp 206°-209° C. A sample recrystallized from acetonitrile was analytically pure, mp 224°-226° C.

Workup

  1. filtrationThe precipitate is filtered off
  2. washrinsed with water
  3. customdried

Sources & evidence

ORD record
ord-914affbb148f404580285c6e9f346ee3
Source dataset
uspto-grants-1996_02
Patent number
US05494927

Reaction notes

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