Methanol → 5-(Benzo[d]isothiazol-6-yl)-1,3,4-thiadiazol-2-amine

HRID 2075385Notes

Reaction equation

CS([C:5]1[S:9][C:8]([C:10]2[CH:18]=[CH:17][C:13]3[CH:14]=[N:15][S:16][C:12]=3[CH:11]=2)=[N:7][N:6]=1)(=O)=O.C([O-])(=O)C.[NH4+:23].CO>C(Cl)Cl>[S:16]1[C:12]2[CH:11]=[C:10]([C:8]3[S:9][C:5]([NH2:23])=[N:6][N:7]=3)[CH:18]=[CH:17][C:13]=2[CH:14]=[N:15]1

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 6-(5-(methylsulfonyl)-1,3,4-thiadiazol-2-yl)benzo[d]isothiazole (0.16 g, 0.54 mmol) and excess ammonium acetate (1.93 mL, 26.9 mmol) was heated in a microwave-safe reaction vessel at 140° C. for 30 minutes under microwave irradiation. The mixture was cooled, 5% MeOH in DCM (with NH3) was added, and the mixture was adsorbed onto silica gel. The residue was purified by flash column chromatography (DCM—10% MeOH in DCM) to obtain the desired product as an off-white solid (89 mg, 71%). LCMS (API-ES) m/z (%): 235.3 (100%, M+H+); 1H-NMR (400 MHz, CD3OD) δ ppm 9.02 (s, 1 H) 8.49 (s, 1 H) 8.25 (d, J=8.53 Hz, 1 H) 7.98 (d, J=9.03 Hz, 1 H).

Workup

temperatureThe mixture was cooled
customThe residue was purified by flash column chromatography (DCM—10% MeOH in DCM)

Sources & evidence

ORD record: ord-4b4f42df17914c7ab2b9d31675f58643
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07919504B2

Reaction notes

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