Methanesulfonyl chloride → HCID 3805968, compound

HRID 1177008Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

Methanesulfonyl chloride (4.93 mL, 63.7 mmol) was added over 5 min to a solution of benzothiazol-6-ylamine (9.58 g, 63.8 mmol) in pyridine (100 mL) at 25° C. The resulting mixture was stirred at 25° C. for 30 min, and then was concentrated in vacuo. The residue was partitioned between 1.0 M aqueous hydrochloric acid solution (150 mL) and ethyl acetate (2×150 mL). The organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. Trituration of the residue with diethyl ether afforded a solid that was collected by vacuum filtration and dried in vacuo to afford the desired product, N-benzothiazol-6-yl-methanesulfonamide (13.3 g, 58.3 mmol, 91% yield) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ: 3.03 (3H, s), 7.36 (1H, dd, J1=2.3 Hz, J2=8.6 Hz), 7.94 (1H, d, J=1.6 Hz), 8.02 (1H, d, J=9.2 Hz), 9.27 (1H, s), 9.95 (1H, s).

Workup

concentrationwas concentrated in vacuo
customThe residue was partitioned between 1.0 M aqueous hydrochloric acid solution (150 mL) and ethyl acetate (2×150 mL)
dry with materialThe organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customTrituration of the residue with diethyl ether afforded a solid
filtrationthat was collected by vacuum filtration
customdried in vacuo

Sources & evidence

ORD record: ord-cc3cfdf51aab46e68a56b07580f57034
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842838B2

Reaction notes

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