Toluene → HCID 86755317, compound

HRID 1387368Notes

Reaction equation

HRID 1387368 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](=[N:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=1[C:41](=[N:44][O:45][CH3:46])[CH:42]=O)[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1>[Cl-].[Na+].O.C(O)CCC>[CH3:46][O:45][N:44]=[C:41]([CH:42]1[NH:9][CH2:10][CH2:11][S:12]1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[CH2:34][O:33][N:32]=[C:21]([CH3:20])[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:29])[F:30])[CH:23]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 86755316HCID 86755316, compound

Product 1

HCID 86755317HCID 86755317, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Toluene (2.5 ml), butanol (2.5 ml), cysteamine hydrochloride (0.29 g, 2.54 mmol) and triethylamine (0.26 g, 2.54 mmol) were added to 2-[(α-methyl-3-trifluoromethylbenzylidene) aminooxymethyl]-α-methoxyiminophenylacetaldehyde (0.48 g, 1.27 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 acetatein-hexane) to give 2-[(α-methyl-3-trifluoromethylbenzylidene)aminooxymethyl]phenyl thiazolidin-2-yl ketone O-methyloxime (0.52 g, yield 93.6%) 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 acetatein-hexane)

Sources & evidence

ORD record
ord-e0bf0d0a6cbe41d78102fd0092d8383b
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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