Methyl iodide → HCID 59853593, compound

HRID 730504Notes

Reaction equation

[H-].[Na+].[S:3]1[C:7]2[CH:8]=[C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1.I[CH3:18]>O1CCCC1>[S:3]1[C:7]2[CH:8]=[C:9]([N:12]([CH3:18])[S:13]([CH3:16])(=[O:14])=[O:15])[CH:10]=[CH:11][C:6]=2[N:5]=[CH:4]1

Participants

Conditions

Temperature: 25 °C

Procedure

Sodium hydride (2.56 g of a 60% dispersion in mineral oil, 64.0 mmol) was added to a solution of N-benzothiazol-6-yl-methanesulfonamide (Example 7a, 13.3 g, 58.2 mmol) in tetrahydrofuran at 0° C. After 15 min, iodomethane (36.2 mL, 581 mmol) was added and the reaction mixture was warmed to 25° C., stirred for 4 h, then was partitioned between 1.0 M aqueous hydrochloric acid solution (300 mL) and ethyl acetate (2×250 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-N-methyl-methanesulfonamide (12.1 g, 50 mmol, 86% yield) as a pink solid. 1H NMR (400 MHz, DMSO-d6) δ: 3.00 (3H, s), 3.31 (3H, s), 7.57 (1H, dd, J1=2.2 Hz, J2=8.7 Hz), 8.07 (1H, d, J=8.5 Hz), 8.23 (1H, d, J=1.7 Hz), 9.40 (1H, s).

Workup

customwas partitioned between 1.0 M aqueous hydrochloric acid solution (300 mL) and ethyl acetate (2×250 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-bdef480d3ac54e09ad8a749691e40e62
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582754B2

Reaction notes

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