Formaldehyde → HCID 18707201, compound

HRID 1421975Notes

Reaction equation

HRID 1421975 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]([OH:24])=[C:20]([CH2:25][CH3:26])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[CH2:27]=O.[ClH:29].[CH3:30][NH:31][CH3:32]>C(O)C>[ClH:29].[ClH:29].[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][C:15]([CH2:30][N:31]([CH3:27])[CH3:32])=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH2:25][CH3:26])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 18707256HCID 18707256, compound

Product 1

HCID 18707201HCID 18707201, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 1 g of 2-(3,4-diethoxyphenyl)-4-(3-ethyl-4-hydroxyphenyl)thiazole, 1 g of paraformaldehyde and 1.1 g of dimethylamine hydrochloride in 20 ml of ethanol was stirred at 100° C. for 4 hours with heating. The solvent was distilled off. The residue was mixed with 20 ml of water and 30 ml of ethyl acetate for extraction and phase separation. The ethyl acetate layer was extracted with 10% hydrochloric acid (20 ml×3). The combined aqueous layer was made basic with 10% sodium hydroxide and extracted with dichloromethane. The extract was washed with 20 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=49/1). The product was dissolved in acetone, mixed with hydrochloric acid-methanol and heated. The resulting crystals were collected by filtration, dried and recrystallized from acetone to obtain 117 mg of 2-(3,4-diethoxyphenyl)-4-(3-ethyl-4-hydroxyphenyl)-5-dimethylaminomethylthiazole dihydrochloride.

Workup

  1. temperaturewith heating
  2. distillationThe solvent was distilled off
  3. additionThe residue was mixed with 20 ml of water and 30 ml of ethyl acetate for extraction and phase separation
  4. extractionThe ethyl acetate layer was extracted with 10% hydrochloric acid (20 ml×3)
  5. extractionextracted with dichloromethane
  6. washThe extract was washed with 20 ml of a saturated aqueous sodium chloride solution
  7. customdried
  8. distillationsubjected to distillation
  9. customto remove the solvent
  10. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=49/1)
  11. dissolutionThe product was dissolved in acetone
  12. additionmixed with hydrochloric acid-methanol
  13. temperatureheated
  14. filtrationThe resulting crystals were collected by filtration
  15. customdried
  16. customrecrystallized from acetone

Sources & evidence

ORD record
ord-0e21e9413cbf426dbbc36a77ed1d7142
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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