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Hydrochloric Acid → 5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-ethyl-4-thiazolidinone

HRID 2941
Notes
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Reaction equation

HRID 2941 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][NH:19][C:18]2=[O:22])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[H-].[Na+].[CH2:25](I)[CH3:26].Cl>O1CCCC1.C(OCC)C.O>[CH3:4][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][CH2:20][N:19]([CH2:25][CH3:26])[C:18]2=[O:22])[CH:8]=[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])[C:10]=1[OH:11])([CH3:1])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 1300035-(3,5-Bis(tert-butyl)-4-hydroxyphenyl)methylene-4-thiazolidinone

Product 1

HCID 537733605-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-3-ethyl-4-thiazolidinone

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 3283Diethyl EtherSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9.58 g of 5-[[3,5-bis(1,1-dimethylethyl) -4-hydroxyphenyl]methylene]-4-thiazolidinone in 150 ml of tetrahydrofuran were added 1.20 g of a 60% dispersion of sodium hydride in mineral oil. After gas evolution ceased, 2.4 ml of ethyl iodide were added and the reaction mixture was stirred for two days under an argon atmosphere. The mixture was heated at reflux for six hours, cooled, diluted with diethyl ether and water, and adjusted to pH 3 with 1N hydrochloric acid. The layers were separated, and the organic layer was washed with a saturated sodium bicarbonate solution followed by a saturated sodium chloride solution. Concentration of the dried organic solution and chromatography of the resulting residue over silica gel eluting with a 10-30% ethyl acetate in hexane gradient provided 3.65 g of the desired title product, m.p. 169°-172.5° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for six hours
  3. temperaturecooled
  4. customThe layers were separated
  5. washthe organic layer was washed with a saturated sodium bicarbonate solution

Sources & evidence

ORD record
ord-99da04be27454cd9bffd7d2ff5f26253
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731336

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes