Toluene → 4-chloro-N-methylbenzothiazolone

HRID 847805Notes

Reaction equation

HRID 847805 reaction equation
[Cl:1][C:2]1[C:7]2[N:8]=[CH:9][S:10](=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:14]1(C)C=CC=CC=1.S(OC)(OC)(=O)=O>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[C:7]2[N:8]([CH3:14])[CH2:9][S:10](=[O:11])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 534006884-Chlorobenzothiazolone

Product 1

HCID 696450104-chloro-N-methylbenzothiazoloneYield 90.3%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

4-chlorobenzothiazolone (9.28 g, 0.05 mole) was dissolved in a solution of sodium hydroxide (3.19 g, 0.075 mole) in water (220 ml), and benzyltriethylammonium chloride (0.34 g, 0.0015 mole) and toluene (80 ml) were added thereto. Dimethyl sulfate (9.40 g, 0.075 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 4 hours, followed by phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 8.97 g of 4-chloro-N-methylbenzothiazolone as pale yellow crystals. Yield 90.3%, purity 96.7%, m.p. 129°-131° C.

Workup

  1. additionwere added
  2. customfollowed by phase-separation
  3. washThe toluene layer was washed once with water
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d646ea01e9074c4ab6ceb304c2449f60
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Reaction notes

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