1,2-Dichloroethane → 4-chloro-N-methylbenzothiazolone

HRID 847806

Reaction equation

HRID 847806 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+].[CH2:14](Cl)CCl.S(OC)(OC)(=O)=O>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 111,2-DichloroethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 534006884-Chlorobenzothiazolone

Product 1

HCID 696450104-chloro-N-methylbenzothiazoloneYield 93.9%

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 (500 ml), and tetra-n-butylammonium bromide (0.48 g, 0.0015 mole) and ethylene dichloride (300 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 1 hour, followed by phase-separation. The ethylene dichloride layer was washed once with water, and the solvent was removed under reduced pressure to obtain 9.37 g of 4-chloro-N-methylbenzothiazolone as pale yellow crystals. Yield 93.9%, purity 98.7%, m.p. 130°-132° C.

Workup

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

Sources & evidence

ORD record
ord-5d1e1d871b804ddda12daf9877af0ddf
Source dataset
uspto-grants-1981_10
Patent number
US04293702

Linked notes

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