Chloroform → 4-chloro-N-methylbenzothiazolone

HRID 847802

Reaction equation

[Cl:1][C:2]1[C:7]2[N:8]=[C:9](OC)S[C:6]=2[CH:5]=[CH:4][CH:3]=1.[S:13]([O:18]C)(OC)(=O)=O.[CH:20](Cl)(Cl)Cl>>[Cl:1][C:2]1[C:7]2[N:8]([CH3:9])[CH2:20][S:13](=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6212Chloroform

HCID 6497Dimethyl Sulfate

HCID 41419694-Chloro-2-methoxybenzothiazole

Product 1

HCID 696450104-chloro-N-methylbenzothiazoloneYield 99.7%

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-chloro-2-methoxybenzothiazole (3.00 g, 0.015 mole) and dimethyl sulfate (95 mg, 7.5×10-4 mole) was heated at 150° C. for 3 hours with stirring. After cooling, the reaction mass was dissolved in chloroform, and the chloroform layer was washed with an aqueous solution saturated with sodium carbonate and then with water. The solvent was removed under reduced pressure to obtain 2.99 g of 4-chloro-N-methylbenzothiazolone as white crystals. Yield 99.7%, purity 99.0%, m.p. 130°-132° C.

Workup

temperatureAfter cooling
washthe chloroform layer was washed with an aqueous solution saturated with sodium carbonate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-3430b6b0385643a59c87c7ea15694002
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04293702

Linked notes

Loading…