Hydrochloric Acid → HCID 18707120, compound

HRID 1489266Notes

Reaction equation

HRID 1489266 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24]COC)=[C:20]([C:28]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:29])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].Cl>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([C:28]([O:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[O:29])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18707224HCID 18707224, compound

Product 1

HCID 18707120HCID 18707120, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol was dissolved 340 mg of 2-(3,4- diethoxyphenyl)-4-(3-nonyloxycarbonyl-4-methoxymethoxyphenyl)thiazole. Thereto was added 2 ml of 10% hydrochloric acid, and the mixture was refluxed for 20 minutes. The solvent was removed by distillation. To the residue were added 40 ml of dichloromethane and 20 ml of water, and phase separation was conducted. The organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was recrystallized from ethanol to obtain 245 mg of 2-(3,4-diethoxyphenyl)-4-(3-nonyloxycarbonyl-4-hydroxyphenyl)thiazole as a white powder.

Workup

  1. temperaturethe mixture was refluxed for 20 minutes
  2. customThe solvent was removed by distillation
  3. additionTo the residue were added
  4. custom40 ml of dichloromethane and 20 ml of water, and phase separation
  5. washThe organic layer was washed with 15 ml of a saturated aqueous sodium chloride solution
  6. customdried
  7. distillationsubjected to distillation
  8. customto remove the solvent
  9. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-a8f6c40b379a4dbfb16c8ceec6ca4aa6
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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