Potassium Carbonate → HCID 20482399, compound

HRID 648211Notes

Reaction equation

HRID 648211 reaction equation
[C:1]([NH:4][C:5]1[S:6][C:7]([Cl:12])=[C:8]([CH2:10]Cl)[N:9]=1)(=[O:3])[CH3:2].[CH:13]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:1]([NH:4][C:5]1[S:6][C:7]([Cl:12])=[C:8]([CH2:10][N:29]2[CH2:30][CH2:31][N:26]([CH:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)[N:9]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 20482441HCID 20482441, compound

Product 1

HCID 20482399HCID 20482399, compoundYield 40.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-acetamido-5-chloro-4-chloromethylthiazole (450 mg), 1-benzhydrylpiperazine (504 mg) and potassium carbonate (276 mg) in N,N-dimethylformamide (3 ml) was stirred at 70° C. for 20 minutes. After the reaction mixture was poured into ice-water, the precipitated crystals were collected by filtration, washed with water and then dried, followed by recrystallization from a mixture of ethyl acetate and n-hexane to obtain crystals (355 mg) of 2-acetamido-5-chloro-4-(4-benzhydrylpiperazin-1-ylmethyl)thiazole, mp 227°-230° C.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. washwashed with water
  3. customdried
  4. customfollowed by recrystallization from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-3dfab01acd024e8abe5de4949a4dcc82
Source dataset
uspto-grants-1983_10
Patent number
US04411900

Reaction notes

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