Water → HCID 53716497, compound

HRID 1534567Notes

Reaction equation

HRID 1534567 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][O:9][N:10]=[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22]Br)[C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O.[I-].[K+]>[CH3:8][O:9][N:10]=[C:11]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

7

Reactant 4

HCID 962WaterHCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 54028047Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

Product 1

HCID 53716497HCID 53716497, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

1.5 g (0.014 mole) of thiophenol and 4 g (0.014 mole) of methyl 2-(bromomethyl)-phenylglyoxylate O-methyloxime (Method 3) are dissolved in 100 ml of acetone. 2.2 g of potassium carbonate and 0.1 g of potassium iodide are added. The stirred mixture is refluxed for 17 hours and then cooled, after which 100 ml of water are added. The aqueous phase is extracted with methylene chloride and the extract is dried over sodium sulfate and evaporated down. The crude product is crystallized by trituration with n-pentane. 2.33 g (55%) of the abovementioned compound are obtained as a colorless solid (mp.=60°-65° C.)

Workup

  1. temperatureThe stirred mixture is refluxed for 17 hours
  2. temperaturecooled
  3. extractionThe aqueous phase is extracted with methylene chloride
  4. dry with materialthe extract is dried over sodium sulfate
  5. customevaporated down
  6. customThe crude product is crystallized by trituration with n-pentane

Sources & evidence

ORD record
ord-d7b3c6435f4044c98dc17e45345624c3
Source dataset
uspto-grants-1992_02
Patent number
US05089528

Reaction notes

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