Dichloromethane → HCID 19757951, compound

HRID 1587408Notes

Reaction equation

HRID 1587408 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([C:23]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[O:24])[S:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[C:31](=[O:34])([O-])O.[Na+].Cl[CH2:37]Cl>>[C:31]([N:28]1[CH2:27][CH2:26][N:25]([C:23]([C:12]2[S:13][C:14]([C:15]3[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=3)=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=3)[N:11]=2)=[O:24])[CH2:30][CH2:29]1)(=[O:34])[CH3:37]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 19757968HCID 19757968, compound

Product 1

HCID 19757951HCID 19757951, compound

Procedure

A mixture of 4,5-bis(4methyoxyphenyl)-2-piperazin-1-ylcarbonylthiazole hydrochloride (0.40 g) in dichloromethane (30 ml) was added to a saturated aqueous solution of sodium hydrogencarbonate, and extracted with dichloromethane. The separated organic layer was washed with brine and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo. The resulting residue was dissolved in a mixture of dichloromethane (10 ml) and triethylamine (0.14 ml). To the mixture was added dropwise a solution of acetyl chloride (0.07 ml) in dichloromethane (5 ml), at 0° to 5° C., and the reaction mixture was stirred at ambient temperature for 30 minutes. The resulting mixture was poured into water, and adjusted to pH 11 with aqueous solution of potassium carbonate, and extracted with dichloromethane. The separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water, dilute hydrochloric acid, water, and brine, and dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The resulting residue was recrystallized from a mixture of isopropyl ether and ethanol to give a crystal of 2-(4acetylpiperazin-1-yl)carbonyl-4,5-bis(4methoxyphenyl)thiazole (0.18 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration
  5. customthe filtrate was evaporated in vacuo
  6. dissolutionThe resulting residue was dissolved in a mixture of dichloromethane (10 ml) and triethylamine (0.14 ml)
  7. additionTo the mixture was added dropwise a solution of acetyl chloride (0.07 ml) in dichloromethane (5 ml)
  8. additionThe resulting mixture was poured into water
  9. extractionextracted with dichloromethane
  10. washThe separated organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, water, dilute hydrochloric acid, water, and brine
  11. dry with materialdried over magnesium sulfate
  12. additiontreated with activated charcoal
  13. filtrationAfter filtration
  14. customthe filtrate was evaporated in vacuo
  15. customThe resulting residue was recrystallized from a mixture of isopropyl ether and ethanol

Sources & evidence

ORD record
ord-5ee41521f599458ba11efe38e2ba7379
Source dataset
uspto-grants-1993_06
Patent number
US05217971

Reaction notes

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