N-Acetylsulfanilyl chloride → N-[4-[(1,3,4-Thiadiazol-2-ylamino)sulfonyl]phenyl]acetamide

HRID 1966878Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)(=[O:9])[CH3:8]>N1C=CC=CC=1.Cl>[S:3]1[CH:4]=[N:5][N:6]=[C:2]1[NH:1][S:17]([C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:7](=[O:9])[CH3:8])=[CH:16][CH:15]=1)(=[O:19])=[O:18]

Participants

Conditions

Temperature: 95 °C

Procedure

2-Amino-1,3,4-thiadiazole (500 mg, 4.95 mmol) was suspended in pyridine (1.26 mL). p-Acetamidobenzenesulfonyl chloride (1.2 g, 5.15 mmol) was added and the mixture was heated to 95° C. for 1 h. The mixture was dissolved in 10% aqueous HCl and extracted with ethyl acetate. The organic extracts were washed with water and dried over anhydrous Na2SO4. Evaporation of the solvent yielded the crude product (1.4 g, 4.7 mmol, 95%). Recrystallization from CH2Cl2/MeOH gave pure product, mp 216-217° C. (lit1 mp 214-215° C.); 1H NMR (250 MHz, CDCl3) δ 2.07 (3, s), 7.73 (4, s), 8.74 (1, s), 10.35 (1, s), 14.35 (1, br s); 13C NMR (62.5 MHz, DMSO) δ 24.2, 118.7, 127.0, 135.6, 143.0, 144.9, 167.2, 169.

Workup

extractionextracted with ethyl acetate
washThe organic extracts were washed with water
dry with materialdried over anhydrous Na2SO4
customEvaporation of the solvent

Sources & evidence

ORD record: ord-61ac95935232490e914d657273988bb1
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420678B2

Reaction notes

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