Water → HCID 59282857, compound

HRID 1965863Notes

Reaction equation

HRID 1965863 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]2[NH:7][C:8](=[O:10])[S:9][C:5]=2[CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C=O)C>[CH2:19]([N:7]1[C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[S:9][C:8]1=[O:10])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 137457066-Methoxy-1,3-benzothiazol-2(3H)-one

Product 1

HCID 59282857HCID 59282857, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-methoxybenzthiazol-2-one (1, 0.036 g, 0.2 mmol), anhydrous K2CO3 (0.110 g, 0.8 mmol, 4 eq) and benzyl bromide (0.035 L, 0.3 mmol, 1.5 eq) was stirred in anhydrous DMF (2 mL) at 120° C. for 2 h. The reaction mixture was cooled and poured in to water, extracted with EtOAc. The EtOAc layer washed with water (2×10 mL), dried over Na2SO4 and evaporated to dryness. The crude mixture was purified by Combiflash, using hexane-ethylacetate (7:3) as a solvent afforded W-124 as a solid (0.037 g, 68%) as colorless oil; 1H NMR (CDCl3): δ 7.36-7.25 (5H, m), 7.0 (1H, d, J=2.4 Hz), 6.85 (1H, d, J=8.8 Hz), 6.77 (1H, dd, J=8.8 and 2.8 Hz), 5.12 (2H, s), 3.79 (3H, s); MS: 274.0 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with EtOAc
  3. washThe EtOAc layer washed with water (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe crude mixture was purified by Combiflash

Sources & evidence

ORD record
ord-14a826eda94a4fd6a31868560b05f6a8
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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