Toluene → HCID 70449161, compound

HRID 847807Notes

Reaction equation

HRID 847807 reaction equation
[CH3:1][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.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][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 70563277HCID 70563277, compound

Product 1

HCID 70449161HCID 70449161, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

4-Methylbenzothiazolone (4.13 g, 0.025 mole) was dissolved in a solution of sodium hydroxide (1.60 g, 0.0375 mole) in water (100 c.c.), and tetra-n-butylammonium bromide (0.24 g, 7.5×10-4 mole) and toluene (40 c.c.) were added thereto. Dimethyl sulfate (4.70 g, 0.0375 mole) was added dropwise thereto at room temperature, and the mixture was stirred at room temperature for 1 hour, followed by phaseseparation. The toluene layer was washed once with water, and the solvent was removed under reduced pressure to obtain 4.31 g of 4-methyl-N-methylbenzothiazolone as white crystals. Yield 96.2%, purity 98.8%, m.p. 122°-124° C.

Workup

  1. additionwere added
  2. washThe toluene layer was washed once with water
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-08e24a32d9f449898f676627cae5ec50
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Reaction notes

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