Sodium Hydroxide → N-methylbenzothiazolone

HRID 326238Notes

Reaction equation

HRID 326238 reaction equation
[S:1]1(=[O:10])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[OH-].[Na+].[CH3:13]OS([O-])(=O)=O>O>[CH3:13][N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1](=[O:10])[CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 4694097Methyl sulfate(1-)HCID 53400715Benzothiazolinone

Product 1

HCID 20026384N-methylbenzothiazolone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2-liter flask, 75.6 g (0.5 mol) of benzothiazolinone are dissolved in a solution containing 20 g of sodium hydroxide (0.5 mol) in approximately 800 cm3 of water. The solution is filtered. With magnetic stirring, 47.5 cm3 of methylsulfate (0.5 mol) are introduced dropwise with a dropping funnel. After the addition, the mixture is left stirring for 20 hours at room temperature. The medium is alkalinized with a slight excess of sodium hydroxide and left stirring for one hour. The precipitate obtained is drained and washed with water until the filtrate is neutral. The product is dried. It is recrystallized in propanol.

Workup

  1. filtrationThe solution is filtered
  2. additionAfter the addition
  3. waitthe mixture is left
  4. waitleft
  5. stirringstirring for one hour
  6. customThe precipitate obtained
  7. washwashed with water until the filtrate
  8. customThe product is dried
  9. customIt is recrystallized in propanol

Sources & evidence

ORD record
ord-728ad984f35c49c0850403d03d2f258b
Source dataset
uspto-grants-1993_12
Patent number
US05268381

Reaction notes

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