Potassium Carbonate → HCID 86683431, compound

HRID 579456Notes

Reaction equation

HRID 579456 reaction equation
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.[CH:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:13]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[S:3][C:4]3[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:18][CH2:17]1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161884471-Isopropyl-piperazine hydrochlorideHCID 451167822-Bromo-1,3-benzothiazol-6-ol

Product 1

HCID 86683431HCID 86683431, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-6-hydroxybenzothiazole (345 mg, 1.5 mmol), 1-isopropyl-piperazine hydrochloride (271 mg, 1.65 mmol) and dry potassium carbonate (828 mg, 6.00 mmol), were dissolved in 6 mL, of dry N,N-dimethylformamide. The resulted pale brown solution was stirred at 100° C. for 18 h in a closed vial. The reaction mixture was evaporated, suspended in 20 mL of water and extracted with dichloromethane (3×15 mL). The combined organic layers were washed with saturated sodium bicarbonate and brine, then dried over MgSO4. After evaporation the residue was purified by column chromatography (Kieselgel 60) using chloroform-methanol 49:1 as the eluent. The title compound (76 mg, 0.27 mmol, 18%) was obtained as a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with dichloromethane (3×15 mL)
  3. washThe combined organic layers were washed with saturated sodium bicarbonate and brine
  4. dry with materialdried over MgSO4
  5. customAfter evaporation the residue
  6. customwas purified by column chromatography (Kieselgel 60)

Sources & evidence

ORD record
ord-e67e41a5abab4f0da95fb83afa0fbbd4
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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