Hydrochloric Acid → N-[4-[[(5-Ethyl-1,3,4-thiadiazol-2-yl)amino]sulfonyl]phenyl]acetamide

HRID 1854273Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([CH2:7][CH3:8])=[N:5][N:6]=1.[C:9]([NH:12][C:13]1[CH:22]=[CH:21][C:16]([S:17](Cl)(=[O:19])=[O:18])=[CH:15][CH:14]=1)(=[O:11])[CH3:10].Cl>N1C=CC=CC=1>[CH2:7]([C:4]1[S:3][C:2]([NH:1][S:17]([C:16]2[CH:15]=[CH:14][C:13]([NH:12][C:9](=[O:11])[CH3:10])=[CH:22][CH:21]=2)(=[O:19])=[O:18])=[N:6][N:5]=1)[CH3:8]

Participants

Conditions

Temperature: 95 °C

Procedure

2-Amino-5-ethyl-1,3,4-thiadiazole (250 mg, 1.93 mmol) was suspended in pyridine (0.5 mL). N-Acetylsulfanilyl chloride (361 mg, 1.54 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 (350 mg, 1.07 mmol, 70%) as a solid, mp 197-198° C.; 1H NMR (500 MHz, DMSO) δ 1.28 (3, t, J=7.0 Hz), 2.07 (3, s), 2.82 (2, q, J=7.0 Hz), 7.72 (4, s), 10.32 (1, s), 13.91 (1, s); 13C NMR (125 MHz, DMSO) δ 12.2, 23.7, 24.1, 48.6, 118.5, 126.9, 135.6, 142.7, 159.8, 167.3, 168.9; MS (LCQ, ESI+) Calculated for C12H15N4O3S2 327.1. found 327.1 (M+H)+; HRMS (FAB+, m/z) Calculated for C12H15N4O3S2 327.0586. found 327.0585 (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-70f37b939fb643c69473b1b2e3d12b29
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962663B2

Reaction notes

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