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

HRID 1065363Notes

Reaction equation

[C:1]1([S:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)(Cl)(=O)=[O:25].C(O)C>C(Cl)Cl>[C:1]1([S:7]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[NH:19][C:18](=[O:23])[CH2:17][CH2:16]3)=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: -70 °C

Procedure

3.3 gm of 6-(4-phenylmercapto-butoxy)-3,4-dihydro-carbostyril were dissolved in 50 ml of methylene chloride, the solution cooled to -70° C., and a solution of 1.5 gm of sulfuryl chloride in 5 ml of methylene chloride was added dropwise. After 15 hours, 20 ml of 95% ethanol were added, and the mixture was heated to room temperature by removing the cooling bath, neutralized with an aqueous sodium carbonate solution. The methylene chloride phase was dried with sodium sulfate, and the solvent was evaporated. The residue was recrystallized from toluene.

Workup

temperaturethe mixture was heated to room temperature
customby removing the cooling bath
dry with materialThe methylene chloride phase was dried with sodium sulfate
customthe solvent was evaporated
customThe residue was recrystallized from toluene

Sources & evidence

ORD record: ord-b0eba3fd16854d37b234589fb94a54f7
Source dataset: uspto-grants-1982_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04329347

Reaction notes

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