Toluene → HCID 53741675, compound

HRID 1387344Notes

Reaction equation

HRID 1387344 reaction equation
Cl.N[CH2:3][CH2:4][SH:5].C1(C)C=CC=CC=1.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])[C:32]#[N:33]>O.O.C([O-])(=O)C.[Zn+2].C([O-])(=O)C.O>[CH3:36][O:35][N:34]=[C:31]([C:32]1[S:5][CH2:4][CH2:3][N:33]=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]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 9082Cysteamine HydrochlorideHCID 54390956HCID 54390956, compound

Product 1

HCID 53741675HCID 53741675, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 2724192Zinc acetate (USP)CatalystHCID 962WaterSolvent

Procedure

2-Aminoethanethiol hydrochloride (2.80 g, 24.6 mmol), zinc acetate dihydrate (600 mg, 2.7 mmol), toluene (12 ml) and triethylamine (3.12 g, 30.8 mmol) were added to 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminophenylacetonitrile (6.00 g, 20.4 mmol), and the mixture was stirred under reflux for 14 hours. After completion of the reaction, water 100 ml) was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium 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 2-thiazolin-2-yl ketone O-methyloxime (5.71 g, 79.0%) as crystals.

Workup

  1. temperatureunder reflux for 14 hours
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-43a46a62c92b4b788a9c004e1402fe88
Source dataset
uspto-grants-2001_07
Patent number
US06268312B1

Reaction notes

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