Potassium Carbonate → HCID 19003518, compound

HRID 2259407Notes

Reaction equation

HRID 2259407 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12]Cl)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH:22]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]2[N:6]([CH2:10][CH2:11][CH2:12][N:38]3[CH2:39][CH2:40][N:35]([CH:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH2:36][CH2:37]3)[C:7](=[O:9])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70048BenzhydrylpiperazineHCID 190035086-Chloro-3-(3-chloropropyl)-2(3H)-benzothiazolone

Product 1

HCID 19003518HCID 19003518, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of compound (X) (3.71 g, 20 mmol), K2CO3 (3.31 g, 24 mmol), 4-benzhydrylpiperazine (XId) (6.06 g, 24 mmol), and KI (3.98 g, 24 mmol) in DMF (20 ml) was stirred at 100° C. for 5 hours, concentrated in vacuo and extracted with dichloromethane. The resulting dichloromethane layer was dried over MgSO4, and subjected to column chromatography on silica gel. The eluate eluted with dichloromethane/ethyl acetate (10/1) was recrystallized from ether to obtain compound (XIId) (5.9 g, yield=61.7% ) as colorless prism-shaped crystals.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with dichloromethane
  3. dry with materialThe resulting dichloromethane layer was dried over MgSO4
  4. washThe eluate eluted with dichloromethane/ethyl acetate (10/1)
  5. customwas recrystallized from ether
  6. customto obtain compound (XIId) (5.9 g, yield=61.7% ) as colorless prism-shaped crystals

Sources & evidence

ORD record
ord-385ec905089443a48d26ac6368a293ad
Source dataset
uspto-grants-1995_12
Patent number
US05473066

Reaction notes

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