Peracetic Acid → 1-Hydroxy-1-methyl-3-[4-(methylsulfinyl)phenyl]urea

HRID 976634Notes

Reaction equation

HRID 976634 reaction equation
C(OO)(=[O:3])C.[OH:6][N:7]([CH3:19])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:17][CH3:18])=[CH:13][CH:12]=1)=[O:9]>C(Cl)Cl.CO.C(OCC)(=O)C.C(O)C>[OH:6][N:7]([CH3:19])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:18])=[O:3])=[CH:13][CH:12]=1)=[O:9]

Participants

6

Reactant 2

HCID 6585Peracetic AcidHCID 115937101-Hydroxy-1-methyl-3-[4-(methylthio)phenyl]urea2×

Product 1

HCID 199673711-Hydroxy-1-methyl-3-[4-(methylsulfinyl)phenyl]ureaYield 53.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 21584252Ethanol ethylacetateSolvent

Procedure

Peracetic acid (1.7 g of 30%, 6.6 mmol) was added dropwise to a cooled (ice/water bath) solution of 1-hydroxy-1-methyl-3-[4-(methylthio)phenyl]urea (Compound 1, 1.4 g, 6.6 mmol) in a mixture of methylene chloride (25 mL) and methanol (10 mL). The solution was stirred with cooling for 15 minutes. The solvent was removed under reduced pressure at 50° C. to provide a white solid. The solid was dissolved in hot ethyl acetate/ethanol, filtered to remove particulates then diluted with ether to provide 0.8 g of the desired product as a white crystalline solid, m.p. 197.8°-198.2° C. Analysis: Calculated for C9H12N2O3S: %C, 47.36; %H, 5.3; %N, 12.27; Found: %C, 47.27; %H, 4.97; %N, 12.26.

Workup

  1. temperaturewith cooling for 15 minutes
  2. customThe solvent was removed under reduced pressure at 50° C.
  3. customto provide a white solid
  4. filtrationfiltered
  5. customto remove particulates
  6. additionthen diluted with ether

Sources & evidence

ORD record
ord-be0326c94d07467299ae5122ddcbdd6f
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Reaction notes

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