2-Chloro-3',4'-dihydroxyacetophenone → 2-(3,4-Dimethoxyphenyl)-4-(3,4-dihydroxyphenyl)thiazole hydrochloride

HRID 1421949

Reaction equation

HRID 1421949 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH2:10][Cl:11])[CH:5]=[CH:6][C:7]=1[OH:8].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:18]([NH2:20])=[S:19]>C(O)C>[ClH:11].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([C:18]2[S:19][CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([OH:1])[CH:3]=3)[N:20]=2)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25]

Participants

4

Reactant 2

HCID 668342-Chloro-3',4'-dihydroxyacetophenoneHCID 27584903,4-Dimethoxythiobenzamide

Product 1

HCID 187073552-(3,4-Dimethoxyphenyl)-4-(3,4-dihydroxyphenyl)thiazole hydrochlorideYield 22.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol were suspended 367 mg of 3',4'-dihydroxy-2-chloroacetophenone and 430 mg of 3,4-dimethoxythiobenzamide. The suspension was refluxed for 3 hours with heating. After cooling, the resulting crystals were collected by filtration, ethanol-washed and dried. The dried material was recrystallized from ethanol to obtain 160 mg of 2-(3,4-dimethoxyphenyl)-4-(3,4-dihydroxyphenyl)thiazole hydrochloride as yellow acicular crystals.

Workup

  1. temperatureThe suspension was refluxed for 3 hours
  2. temperaturewith heating
  3. temperatureAfter cooling
  4. filtrationthe resulting crystals were collected by filtration, ethanol-
  5. washwashed
  6. customdried
  7. customThe dried material was recrystallized from ethanol

Sources & evidence

ORD record
ord-6114db3fffff415281ee0e1682dfb883
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Linked notes

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