Sodium Hydroxide → 2-Methyl-6-acetoxyethylbenzothiazole

HRID 369566Notes

Reaction equation

HRID 369566 reaction equation
[OH-].[Na+].[C:3]([O:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[S:18])[CH3:17])=[CH:11][CH:10]=1)(=[O:5])[CH3:4]>O.ClCCl>[CH3:17][C:16]1[S:18][C:13]2[CH:14]=[C:9]([CH2:8][CH2:7][O:6][C:3](=[O:5])[CH3:4])[CH:10]=[CH:11][C:12]=2[N:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 232822924-Thioacetamidophenethyl Acetate

Product 1

HCID 543970292-Methyl-6-acetoxyethylbenzothiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

K3Fe(CN)6 (7.6 g, 23.1 mmol) was dissolved in water (18 ml) and then mixed with 50 ml 2% NaOH aqueous solution. 4-Thioacetamidophenethyl acetate (1.0 g, 4.1 mmol) was dissolved in dichloromethane (50 ml) and then added to the K3Fe(CN)6 solution. The reaction mixture was stirred at room temperature for 1 hr. The organic layer was separated by a separatory funnel, washed with water, and then dried over anhydrous sodium sulfate. The dried solution was concentrated and then purified by flash silica gel chromatography. Yield: 0.6 g (61%).

Workup

  1. customThe organic layer was separated by a separatory funnel
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe dried solution was concentrated
  5. custompurified by flash silica gel chromatography

Sources & evidence

ORD record
ord-d1778fbb395a440bb544c4f02c8ff861
Source dataset
uspto-grants-2000_10
Patent number
US06140051

Reaction notes

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