Reaktion #353652

ord-6044b58b956f4f54b6d25cf4b9ff0156

Reaktionsgleichung

COc1cc2c(c(C(C)C)c1OC)C(=O)NS2(=O)=O
4-isopropyl-5,6-dimethoxysaccharin
COc1cc(S(N)(=O)=O)c(C(=O)N(C)C)c(C(C)C)c1OC
2-aminosulfonyl-4,5-dimethoxy-6-isopropyl-N,N-dimethylbenzamide
COc1cc2c(c(C(C)C)c1OC)C(=O)N(CSc1ccccc1)S2(=O)=O
2-phenylthiomethyl-4-isopropyl-5,6-dimethoxysaccharin
O=S(=O)(Cl)Cl
sulfuryl chloride
ClCSc1ccccc1
chloromethyl phenyl sulfide
→
COc1cc2c(c(C(C)C)c1OC)C(=O)N(CCl)S2(=O)=O
2-chloromethyl-4-isopropyl-5,6-dimethoxysaccharin
Ausbeute 85.0%

Edukte

COc1cc2c(c(C(C)C)c1OC)C(=O)NS2(=O)=O
4-isopropyl-5,6-dimethoxysaccharin
COc1cc(S(N)(=O)=O)c(C(=O)N(C)C)c(C(C)C)c1OC
2-aminosulfonyl-4,5-dimethoxy-6-isopropyl-N,N-dimethylbenzamide
COc1cc2c(c(C(C)C)c1OC)C(=O)N(CSc1ccccc1)S2(=O)=O
2-phenylthiomethyl-4-isopropyl-5,6-dimethoxysaccharin
O=S(=O)(Cl)Cl
sulfuryl chloride
ClCSc1ccccc1
chloromethyl phenyl sulfide

Reagenzien

Keine

Lösungsmittel

CCCCCC.CCOC(C)=O
ethyl acetate hexane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigegave

Vorschrift

By the method of Example 22A 2-aminosulfonyl-4,5-dimethoxy-6-isopropyl-N,N-dimethylbenzamide (10.75 g) was prepared and cyclized to 4-isopropyl-5,6-dimethoxysaccharin (mp 186°-188° C. from ether-hexane), phenylthiomethylation of part (5 g) of which with chloromethyl phenyl sulfide (2.48 mL) gave 2-phenylthiomethyl-4-isopropyl-5,6-dimethoxysaccharin (4.07 g), reaction of which with sulfuryl chloride (three molar equivalents) gave 2-chloromethyl-4-isopropyl-5,6-dimethoxysaccharin, 85% yield, mp 117°-119° C. from ethyl acetate-hexane.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05650422uspto-grants-1997_07