2,5-Dichlorobenzenethiol → HCID 20539997, compound

HRID 1065392Notes

Reaction equation

HRID 1065392 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2.C[O-].[K+].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[SH:29]>CO>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[S:29][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 799652,5-DichlorobenzenethiolHCID 131098086-(4-Bromobutoxy)-3,4-dihydro-carbostyrilHCID 23664618Potassium methoxide

Product 1

HCID 20539997HCID 20539997, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

8.94 gm (0.03 mol) of 6-(4-bromo-butoxy)-3,4-dihydro-carbostyril (m.p. 142°-147° C.) were added to a solution of 2.21 gm (0.0315 mol) of potassium methylate and 5.76 gm (0.0315mol) of 98% 2,5-dichloro-thiophenol in 54 ml of methanol. The mixture was refluxed, whereupon at first a clear solution was obtained. After 5 minutes so much crystalline reaction product was separated out that the reaction mixture solidified into a barely stirrable crystal slurry. After one hour the mixture was cooled to room temperature, suction-filtered and the filter cake was recrystallized from ethanol. Colorless crystals with a melting point of 133°-134° C. were obtained.

Workup

  1. temperatureThe mixture was refluxed
  2. customwhereupon at first a clear solution was obtained
  3. customAfter 5 minutes so much crystalline reaction product was separated out that the reaction mixture
  4. filtrationsuction-filtered
  5. customthe filter cake was recrystallized from ethanol
  6. customColorless crystals with a melting point of 133°-134° C. were obtained

Sources & evidence

ORD record
ord-edff6808e07b4507b83a2b852b446b8b
Source dataset
uspto-grants-1982_05
Patent number
US04329347

Reaction notes

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