Toluene → HCID 53741675, compound

HRID 279458Notes

Reaction equation

HRID 279458 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-12ba8887ab8b4ad481f423354f700955
Source dataset
uspto-grants-2002_03
Patent number
US06362212B1

Reaction notes

Loading…