Hydrochloric Acid → HCID 1164242, compound

HRID 1966892Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])=[N:5][N:6]=1.[C:11]([NH:14][C:15]1[CH:24]=[CH:23][C:18]([S:19](Cl)(=[O:21])=[O:20])=[CH:17][CH:16]=1)(=[O:13])[CH3:12].Cl>N1C=CC=CC=1>[C:7]([C:4]1[S:3][C:2]([NH:1][S:19]([C:18]2[CH:17]=[CH:16][C:15]([NH:14][C:11](=[O:13])[CH3:12])=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[N:6][N:5]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 95 °C

Procedure

2-Amino-5-tert-butyl-1,3,4-thiadiazole (1.0 g, 6.36 mmol) was suspended in pyridine (1.6 mL). N-Acetylsulfanilyl chloride (1.9 g, 5.1 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 (3×65 mL), brine (3×65 mL), dried over anhydrous Na2SO4, filtered, and volatiles evaporated. The residue was crystallized from MeOH to give the product (1.59 mg, 4.3 mmol, 84%) as a solid, mp 137-138° C.; 1H NMR (500 MHz, DMSO) δ 1.28 (9, t, J=7.0 Hz), 2.08 (3, s), 7.73 (2, d, J=8.5 Hz), 7.78 (2, d, J=8.5 Hz), 10.48 (1, s), 14.00 (1, brs); 13C NMR (125 MHz, DMSO) δ 24.1, 29.3, 36.1, 118.6, 126.8, 135.6, 142.8, 166.9, 167.2, 169.0; MS (LCQ, ESI+) Calculated for C14H19N4O3S2 355.1, found 355.1 (M+H)+; HRMS (FAB+, m/z) Calculated for C14H19N4O3S2 355.0899, found 355.0900 (M+H)+.

Workup

extractionthe mixture extracted with ethyl acetate
washThe organic extracts were washed with water (3×65 mL), brine (3×65 mL)
dry with materialdried over anhydrous Na2SO4
filtrationfiltered
customvolatiles evaporated
customThe residue was crystallized from MeOH

Sources & evidence

ORD record: ord-45365566a3544465829b56ed4c154a3a
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420678B2

Reaction notes

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