6-[4-(3,4-dichloro-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one → 6-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

HRID 463075Notes

Reaction equation

HRID 463075 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]3[NH:23][C:22](=[O:24])[O:21][C:20]([CH3:26])([CH3:25])[C:19]=3[CH:27]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].I([O-])(=O)(=O)=[O:29].[Na+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:16]=[CH:17][C:18]3[NH:23][C:22](=[O:24])[O:21][C:20]([CH3:25])([CH3:26])[C:19]=3[CH:27]=2)=[O:29])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 132540186-[4-(3,4-dichloro-phenylmercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-oneHCID 23667635Sodium periodate

Product 1

HCID 132539416-[4-(3,4-Dichloro-phenylsulfinyl)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

An amount of 2.14 gm (0.005 mol) of 6-[4-(3,4-dichlorophenyl-mercapto)-butoxy]-4,4-dimethyl-4H-3,1-benzoxazin-2-one is dissolved in 50 ml of methanol, mixed with a solution of 1.3 gm (0.06 mol) of sodium metaperiodate in 10 ml of water, and stirred for two hours at ambient temperature. Then, the mixture is refluxed for three hours, the volume of the reaction mixture is reduced by evaporation to about three-quarters, and water is added. The oil precipitated is separated by decanting of the solvent and is taken up in hot isopropanol/disiopropylether. Upon cooling, crystals are obtained which have a melting point of 138°-139° C.

Workup

  1. temperatureThen, the mixture is refluxed for three hours
  2. customthe volume of the reaction mixture is reduced by evaporation to about three-quarters, and water
  3. additionis added
  4. customThe oil precipitated
  5. customis separated
  6. customby decanting of the solvent
  7. temperatureUpon cooling
  8. customcrystals are obtained which

Sources & evidence

ORD record
ord-37a0f27f08194f5491fecc3e74d8b96c
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Reaction notes

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