Hydrochloric Acid → HCID 18707129, compound

HRID 1699557Notes

Reaction equation

HRID 1699557 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[S:11][CH:12]=2)=[CH:4][CH:3]=1.[CH2:23]=O.[CH3:25][N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.[ClH:32]>C(O)C>[ClH:32].[ClH:32].[ClH:32].[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=3)[S:11][CH:12]=2)=[CH:4][C:3]=1[CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH3:23])[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 531671-MethylpiperazineHCID 18707166HCID 18707166, compound

Product 1

HCID 18707129HCID 18707129, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

In 25 ml of ethanol were suspended 0.5 g of 4-(4-hydroxyphenyl)-2-(3,4-dimethoxyphenyl)thiazole, 1 g of paraformaldehyde and 0.5 g of N-methylpiperazine. The suspension was refluxed for 8 hours with heating. The reaction mixture was subjected to distillation under reduced pressure to remove the solvent. The residue was purified by silica get column chromatography (eluent: dichloromethane/methanol=49/1 by v/v) and dissolved in 10 ml of ethanol. Thereto was added 0.5 ml of ethanol saturated with hydrogen chloride gas, and the mixture was allowed to stand. The resulting crystals were collected by filtration, dried and recrystallized from ethanol to obtain 0.2 g of 4-[4-hydroxy-3-(4-methyl-1-piperazinylmethyl)phenyl]-2-(3,4-dimethoxyphenyl)thiazole trihydrochloride.

Workup

  1. temperatureThe suspension was refluxed for 8 hours
  2. temperaturewith heating
  3. distillationThe reaction mixture was subjected to distillation under reduced pressure
  4. customto remove the solvent
  5. customThe residue was purified by silica
  6. customget column chromatography (eluent: dichloromethane/methanol=49/1 by v/v)
  7. filtrationThe resulting crystals were collected by filtration
  8. customdried
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-44cff86b067443b0b0fc983c128f0b19
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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