Ethanol → HCID 18707326, compound

HRID 1421970Notes

Reaction equation

HRID 1421970 reaction equation
[OH-:1].[K+].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([S:26]C(N(C)C)=O)=[C:22](C(OC)=O)[CH:21]=3)[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4].[CH2:36]([OH:38])C>>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:21]=[CH:22][C:23]([SH:26])=[CH:24][C:25]=3[C:36]([OH:38])=[O:1])[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 18707175HCID 18707175, compound

Product 1

HCID 18707326HCID 18707326, compound

Procedure

1 ml of 10% potassium hydroxide was added to a solution of 250 mg of 2-(3,4-diethoxyphenyl-4-(4-dimethylaminocarbonylthio-3-methoxycarbonylphenyl )thiazole in 5 ml of ethanol. The mixture was refluxed for 8 hours with heating. The solvent was removed by distillation. The residue was extracted with 40 ml of hot ethyl acetate. The extract was made acidic with 10% hydrochloric acid, washed with 5 ml of water and 10 ml of a saturated aqueous sodium chloride solution, and dried. The solvent was removed by distillation. The residue was recrystallized from dioxane-ethanol to obtain 130 mg of 2-(3,4-diethoxyphenyl)-4-(4-mercapto-2-carboxyphenyl)thiazole.

Workup

  1. temperatureThe mixture was refluxed for 8 hours
  2. temperaturewith heating
  3. customThe solvent was removed by distillation
  4. extractionThe residue was extracted with 40 ml of hot ethyl acetate
  5. washwashed with 5 ml of water and 10 ml of a saturated aqueous sodium chloride solution
  6. customdried
  7. customThe solvent was removed by distillation
  8. customThe residue was recrystallized from dioxane-ethanol

Sources & evidence

ORD record
ord-2766b3188d0f4bee89e9f6f860e52edf
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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