Hydrogen Peroxide → 6-(4-Phenylsulfinyl-butoxy)-3,4-dihydro-carbostyril

HRID 1065311Notes

Reaction equation

HRID 1065311 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[K+].[K+].[C:19]1([S:25]([CH2:27][CH2:28][CH2:29][CH2:30]Br)=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(S)C=CC=CC=1.BrCCCCBr.OO>CS(C)=O.C(O)(=O)C.O>[C:19]1([S:25]([CH2:27][CH2:28][CH2:29][CH2:30][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

10

Reactant 6

HCID 784Hydrogen PeroxideHCID 7969ThiophenolHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 545301224-Phenylsulfinylbutylbromide

Product 1

HCID 131383416-(4-Phenylsulfinyl-butoxy)-3,4-dihydro-carbostyril

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

32.6 gm (0.2 mol) of 6-hydroxy-3,4-dihydro-carbostyril [see F. F. Mayer et al., Ber. Dtsch. Chem. Ges. 60, 858 (1927)] and 27.6 gm (0.2 mol) of potassium carbonate were stirred for 5 minutes in 600 ml of dimethylsulfoxide which had been dried over a molecular sieve, and then 52.2 gm of 4-phenylsulfinyl-butyl bromide (0.2 mol) (prepared from thiophenol and 1,4-dibromo-butane and subsequent oxidation with hydrogen peroxide in glacial acetic acid analogous to Example 2; oily substance, solidified upon standing in the refrigerator) were added. After stirring it for 15 hours at 25° C., the reaction mixture was poured into 6 liters of water. After stirring the aqueous mixture for 30 minutes more, the precipitated product was suction-filtered off and thoroughly washed with water. After drying, the filter cake was recrystallized from about 600 ml of xylene in the presence of charcoal. White crystals with a melting point of 144.5°-145.5° C. were obtained.

Workup

  1. customhad been dried over a molecular sieve
  2. additionwere added
  3. stirringAfter stirring the aqueous mixture for 30 minutes more
  4. filtrationthe precipitated product was suction-filtered off
  5. washthoroughly washed with water
  6. customAfter drying
  7. customthe filter cake was recrystallized from about 600 ml of xylene in the presence of charcoal
  8. customWhite crystals with a melting point of 144.5°-145.5° C. were obtained

Sources & evidence

ORD record
ord-813757f1bf554df4b45e6958d15c5ea1
Source dataset
uspto-grants-1982_05
Patent number
US04329347

Reaction notes

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