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

HRID 1004383Notes

Reaction equation

HRID 1004383 reaction equation
C1(C)C=CC=CC=1.C(O)CCC.Cl.[NH2:14][CH2:15][CH2:16][SH:17].[CH3:18][C:19]1[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][C:20]=1[O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](=[N:32][O:33][CH3:34])[CH:30]=O>[Cl-].[Na+].O.C(N(CC)CC)C>[CH3:34][O:33][N:32]=[C:29]([CH:30]1[NH:14][CH2:15][CH2:16][S:17]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][O:21][C:20]1[CH:35]=[C:36]([CH3:39])[CH:37]=[CH:38][C:19]=1[CH3:18]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 1140TolueneHCID 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 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Toluene (3 ml), butanol (3 ml), cysteamine hydrochloride (0.34 g, 3.0 mmol) and triethylamine (0.42 ml, 3 =mol) 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-1cdf6cd10fdd4b43a1699ed27e5b4bf2
Source dataset
uspto-grants-2000_04
Patent number
US06048885

Reaction notes

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