Water → 3-Methoxymethyl-5-[(4-methylphenyl)-sulfonyl]-1,2,4-thiadiazole

HRID 1416320Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]#[N:12])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:13][O:14][CH2:15][C:16]1OC(=O)[S:18][N:17]=1.O>CCCCCCCCCCCC>[CH3:13][O:14][CH2:15][C:16]1[N:12]=[C:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])[S:18][N:17]=1

Participants

Conditions

Temperature: 150 °C

Procedure

4-Methylbenzenesulfonyl cyanide (16.26 g) was added to an emulsion of 5-methoxymethyl-1,3,4-oxathiazol-2-one (6.6 g) in dodecane (60 cm3). The reaction mixture was stirred and heated at 150° C. for 18 hours, then cooled. Water was added and the product extracted into ethyl acetate. The combined organic phases were dried (MgSO4) and ethyl acetate was removed by evaporation under reduced pressure. The residue separated into a brown liquid and a clear dodecane layer which was removed and discarded. Chromatography of the brown liquid on silica gel (Sorbsil C30) using 3:7 ethyl acetate:hexane as eluant give a pale orange oil which solidified on standing (6.94 g). M+ =284; 1H NMR: δ 2.40(3H,s); 3.45(3H,s); 4.7(2H,s); 7.4(2H,d); 8.0(2H,d); (mp 43.4-45-4° C.).

Workup

temperaturecooled
extractionthe product extracted into ethyl acetate
dry with materialThe combined organic phases were dried (MgSO4) and ethyl acetate
customwas removed by evaporation under reduced pressure
customThe residue separated into a brown liquid
customa clear dodecane layer which was removed
customhexane as eluant give a pale orange oil which
custom(mp 43.4-45-4° C.)

Sources & evidence

ORD record: ord-1870628798e8491aad2820e66a60204b
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05912243

Reaction notes

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