Toluene → 4-chloro-N-methylbenzothiazolone

HRID 847803Notes

Reaction equation

HRID 847803 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.CI>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[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 6328Methyl iodideHCID 14798Sodium HydroxideHCID 534006884-Chlorobenzothiazolone

Product 1

HCID 696450104-chloro-N-methylbenzothiazoloneYield 96%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 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 tetra-n-butylammonium bromide (0.48 g, 0.0015 mole) and toluene (80 ml) were added thereto. Methyl iodide (11.21 g, 0.075 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 30 minutes and then at 50° to 60° C. for 1 hour, followed by cooling and phase-separation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 9.58 g of 4-chloro-N-methylbenzothiazolone as pale yellow crystals. Yield 96.0%, purity 99.3%, m.p. 130°-132° C.

Workup

  1. additionwere added
  2. waitat 50° to 60° C. for 1 hour
  3. temperatureby cooling
  4. customphase-separation
  5. washThe toluene layer was washed once with water
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b81c8edefd514e0a93afb0a4c8545220
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Reaction notes

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