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

HRID 847806

Reaktionsgleichung

Reaktionsgleichung von HRID 847806
[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

Komponenten

7

Edukt 4

HCID 111,2-DichloroethaneHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 534006884-Chlorobenzothiazolone

Produkt 1

HCID 696450104-chloro-N-methylbenzothiazoloneAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-5d1e1d871b804ddda12daf9877af0ddf
Quelldatensatz
uspto-grants-1981_10
Patentnummer
US04293702

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