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Toluene → 2-(2,5-dimethylphenoxymethyl)phenyl thiazolidin-2-yl ketone O-methyloxime

HRID 1387359
Notes
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Reaction equation

HRID 1387359 reaction equation
C1(C)C=CC=CC=1.Cl.[NH2:9][CH2:10][CH2:11][SH:12].C(N(CC)CC)C.[CH3:20][C:21]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:22]=1[O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:31](=[N:34][O:35][CH3:36])[CH:32]=O>[Cl-].[Na+].O.C(O)CCC>[CH3:36][O:35][N:34]=[C:31]([CH:32]1[NH:9][CH2:10][CH2:11][S:12]1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][O:23][C:22]1[CH:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:21]=1[CH3:20]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 538610512-(2,5-Dimethylphenoxymethyl)-alpha-methoxyiminophenylacetaldehyde

Product 1

HCID 545398812-(2,5-dimethylphenoxymethyl)phenyl thiazolidin-2-yl ketone O-methyloximeYield 91.6%

Reagents, catalysts & solvents 2

HCID 263
1-Butanol
Solvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

Toluene (3 ml), butanol (3 ml), cysteamine hydrochloride (0.34 g, 3.0 mmol) and triethylamine (0.42 ml, 3 mmol) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetoaldehyde (0.45 g, 1.5 mmol), and the mixture was stirred at room temperature for 1 hour. After completion of the reaction, half-saturated brine (100 ml) was added, and the mixture was extracted with dichloromethane (50 ml) twice. The extracts were dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)phenyl thiazolidin-2-yl ketone O-methyloxime (0.49 g, yield 91.6%) as a colorless oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane (50 ml) twice
  3. dry with materialThe extracts were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-3f37bb35794442a9b2e8dafa0a5b7931
Source dataset
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06268312B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes