Water → 4-Methoxy-2-(methylthio)benzo[d]thiazole

HRID 1242038Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:8]2[N:9]=[CH:10][S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[Li]CCCC.[CH3:17][S:18]SC.O>C1COCC1>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([S:18][CH3:17])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 4-methoxybenzothiazole (495 mg, 3.0 mmol) in anhydrous THF (12 mL) at −78° C. was added BuLi (2.5 mL, 1.6M in hexanes, 4.0 mmol) dropwise. The resulting red solution was stirred at −78° C. for 2 h under N2. Methyl disulfide (0.55 mL, 6.0 mmol) was added dropwise at −78° C. and the mixture was allowed to warm to ambient temperature overnight. The reaction mixture was combined with water and then extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a yellow oil (632 mg, 100%), which solidified upon standing and was used without purification. 1H-NMR (CDCl3): δ 7.35 (1H, d), 7.24 (1H, q), 6.86 (1H, d), 4.06 (3H, s), 2.79 (3H, s).

Workup

temperatureto warm to ambient temperature overnight
extractionextracted with EtOAc
washThe combined extracts were washed with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-6e7146736b7c47bd97aa6f08fff6a0c5
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115640B2

Reaction notes

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