Hydrochloric Acid → N-(4-(((5-Methyl-1,3,4-thiadiazol-2-yl)amino)sulphonyl)phenyl)acetamide

HRID 1854270Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[N:5][N:6]=1.[C:8]([NH:11][C:12]1[CH:21]=[CH:20][C:15]([S:16](Cl)(=[O:18])=[O:17])=[CH:14][CH:13]=1)(=[O:10])[CH3:9].Cl>N1C=CC=CC=1>[CH3:7][C:4]1[S:3][C:2]([NH:1][S:16]([C:15]2[CH:14]=[CH:13][C:12]([NH:11][C:8](=[O:10])[CH3:9])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[N:6][N:5]=1

Participants

Conditions

Temperature: 95 °C

Procedure

2-Amino-5-methyl-1,3,4-thiadiazole (250 mg, 2.19 mmol) was suspended in pyridine (0.5 mL). N-Acetylsulfanilyl chloride (410 mg, 1.75 mmol) was added slowly at 0° C. The reaction mixture was then heated to 95° C. and was stirred for 1 h. The reaction mixture was then added to aqueous 3N HCl and the mixture extracted with ethyl acetate. The organic extracts were washed with water (3×20 mL), brine (3×20 mL), dried over anhydrous Na2SO4, filtered, and volatiles evaporated. The residue was crystallized from MeOH to give the product (491 mg, 1.6 mmol, 97%) as a solid, mp 239-240° C.; 1H NMR (500 MHz, DMSO) δ 2.07 (3, s), 2.44 (3, s), 7.74 (4, s), 10.82 (1, s), 13.85 (1, s); 13C NMR (125 MHz, DMSO) δ 16.1, 24.1, 118.6, 126.9, 135.7, 142.8, 154.3, 167.7, 168.9; MS (ESI+, m/z) Calculated for C11H13N4O3S2 313.0. found 313.0 (M+H)+; HRMS (FAB+, m/z) Calculated for C11H13N4O3S2 313.0429. found 313.0428 (M+H)+.

Workup

extractionthe mixture extracted with ethyl acetate
washThe organic extracts were washed with water (3×20 mL), brine (3×20 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
customvolatiles evaporated
customThe residue was crystallized from MeOH

Sources & evidence

ORD record: ord-3504459648fe45079d4289a0db974a74
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962663B2

Reaction notes

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