Water → 2-{3-[2-(Acetylamino)-1,3-thiazol-4-yl]phenyl}ethyl methanesulfonate

HRID 2117961Notes

Reaction equation

[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C.O>C(Cl)Cl>[CH3:19][S:20]([O:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)[CH:5]=1)(=[O:22])=[O:21]

Participants

Conditions

Temperature: 25 °C

Procedure

To a suspension of N-{4-[3-(2-hydroxyethyl)phenyl]-1,3-thiazol-2-yl}acetamide (300 mg) in CH2Cl2 (10 ml) were added methansulfonyl chloride (106 μl) and triethylamine (207 μl) at 5° C. The mixture was stirred at 25° C. for 2 h. The reaction mixture was poured into water and extracted with dichloromethane. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. Resulting residue was purified by silica gel column chromatography with n-hexane and ethyl acetate (1:1) as an eluent to give 2-{3-[2-(acetylamino)-1,3-thiazol-4-yl]phenyl}ethyl methanesulfonate (388 mg) as a colorless solid.

Workup

extractionextracted with dichloromethane
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated under reduced pressure
customResulting residue was purified by silica gel column chromatography with n-hexane and ethyl acetate (1:1) as an eluent

Sources & evidence

ORD record: ord-578920d6d1d44a1b9ac34cf2f26872b6
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442715B2

Reaction notes

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