Thiophenol → 6-(2-Hydroxy-3-phenylmercapto-propoxy)-3,4-dihydro-carbostyril

HRID 1065352Notes

Reaction equation

HRID 1065352 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[K+].[O:11]1[CH2:26][CH:12]1[CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH2:19][CH2:18]2>CO>[OH:11][CH:12]([CH2:26][S:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:13][O:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][C:20](=[O:25])[CH2:19][CH2:18]2

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 145174016-(Oxiran-2-ylmethoxy)-3,4-dihydroquinolin-2(1H)-oneHCID 23664618Potassium methoxide

Product 1

HCID 540477126-(2-Hydroxy-3-phenylmercapto-propoxy)-3,4-dihydro-carbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4.11 gm (0.04 mol) of thiophenol were added to a suspension of 2.10 gm (0.03 mol) of potassium methylate in 40 ml of methanol, whereby a clear solution was obtained. Then, 4.38 gm of 6-(2,3-epoxy-propoxy)-3,4-dihydro-carbostyril (m.p. 125°-128° C.) were added while stirring, which also dissolved, accompanied by slight generation of heat. After 5 minutes the separation of a white crystal slurry started. After standing overnight, the crystals were suction-filtered off and recrystallized from a little methanol. White crystals with a melting point of 148°-149° C. were obtained.

Workup

  1. customwas obtained
  2. dissolutionwhich also dissolved
  3. temperatureof heat
  4. customAfter 5 minutes the separation of a white crystal slurry
  5. filtrationthe crystals were suction-filtered off
  6. customrecrystallized from a little methanol
  7. customWhite crystals with a melting point of 148°-149° C. were obtained

Sources & evidence

ORD record
ord-4da1b7fbd4404cb98eb198e36faa6d4f
Source dataset
uspto-grants-1982_05
Patent number
US04329347

Reaction notes

Loading…