Hydrochloric Acid → HCID 20482435, compound

HRID 648216Notes

Reaction equation

HRID 648216 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][N:8]2[CH2:13][CH2:12][N:11]([CH:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[N:6]=1.[C:27]([Cl:31])(=[O:30])[CH2:28][CH3:29].[ClH:32]>O1CCCC1.N1C=CC=CC=1>[ClH:31].[ClH:32].[CH:14]([N:11]1[CH2:12][CH2:13][N:8]([CH2:7][C:5]2[N:6]=[C:2]([NH:1][C:27](=[O:30])[CH2:28][CH3:29])[S:3][CH:4]=2)[CH2:9][CH2:10]1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 62324Propionyl chlorideHCID 13386489HCID 13386489, compound

Product 1

HCID 20482435HCID 20482435, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-4-(4-benzhydrylpiperazin-1-ylmethyl)thiazole (1.1 g) in tetrahydrofuran (10 ml) and pyridine (5 ml) was added dropwise propionyl chloride (0.92 ml) under ice-cooling with stirring, and the stirring was continued at the same temperature for an hour. After concentration of the reaction mixture the residue was extracted with ethyl acetate, followed by washing with an aqueous solution of sodium bicarbonate and water and drying over anhydrous magnesium sulfate. Removal of the solvent gave an oil, which was transformed into its hydrochloride in a conventional manner, followed by recrystallization from a mixture of methanol and diethyl ether to obtain white crystals (0.8 g) of 4-(4-benzhydrylpiperazin-1-ylmethyl)-2-propionamidothiazole dihydrochloride, mp 181°-184° C. (dec.).

Workup

  1. temperaturecooling
  2. waitthe stirring was continued at the same temperature for an hour
  3. extractionAfter concentration of the reaction mixture the residue was extracted with ethyl acetate
  4. washby washing with an aqueous solution of sodium bicarbonate and water
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. customRemoval of the solvent
  7. customgave an oil, which
  8. customfollowed by recrystallization from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-094ecc2c45c141ec9a45bde223fd46b2
Source dataset
uspto-grants-1983_10
Patent number
US04411900

Reaction notes

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