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

HRID 1065363
Notes
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Reaction equation

HRID 1065363 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 702EthanolHCID 24648Sulfuryl chlorideHCID 248459066-(4-Phenylmercapto-butoxy)-3,4-dihydro-carbostyril

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. temperaturethe mixture was heated to room temperature
  2. customby removing the cooling bath
  3. dry with materialThe methylene chloride phase was dried with sodium sulfate
  4. customthe solvent was evaporated
  5. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes