p-Toluenesulphonyl cyanide → HCID 66899663, compound

HRID 19103Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2OC(=O)[S:10][N:9]=2)=[CH:5][CH:4]=1.[C:16]1([CH3:27])[CH:21]=[CH:20][C:19]([S:22]([C:25]#[N:26])(=[O:24])=[O:23])=[CH:18][CH:17]=1>C1(C)C=C(C)C=C(C)C=1>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][C:8]2[N:26]=[C:25]([S:22]([C:19]3[CH:18]=[CH:17][C:16]([CH3:27])=[CH:21][CH:20]=3)(=[O:23])=[O:24])[S:10][N:9]=2)=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a suspension of 5-(4-methoxy-benzyl)-[1,3,4]oxathiazol-2-one (335 mg, 1.50 mmol) in mesitylene (3 mL) was added 4-toluenesulfonylcyanide (572 mg, 3.00 mmol) and the resulting mixture heated to 150° C. for 135 min. The resulting brown solution was cooled and purified by flash chromatography (silica gel, 0% to 33% ethyl acetate/hexanes) which afforded 3-(4-methoxy-benzyl)-5-(toluene-4-sulfonyl)-[1,2,4]thiadiazole (462 mg, 86%) as a dark yellow solid.

Workup

temperatureThe resulting brown solution was cooled
custompurified by flash chromatography (silica gel, 0% to 33% ethyl acetate/hexanes) which

Sources & evidence

ORD record: ord-8849d89a86104cefad7c6dec994f2ea9
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07741327B2

Reaction notes

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