Acetyl chloride → 2-(4-Nitrophenyl)benzo[d]thiazol-6-yl acetate

HRID 643646Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[C:22](Cl)(=[O:24])[CH3:23]>C1COCC1>[C:22]([O:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[S:11][C:12]=2[CH:18]=1)(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

Under N2, 24 (4.0 mmol) was dissolved in THF (100 ml) and, at 0° C., NaH (8.2 mmol) was slowly added. The mixture was stirred for 30 min at 0° C. and acetyl chloride (6.0 mmol) was added dropwise. The resulting mixture was then stirred at room temperature overnight. The reaction was hydrolyzed and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and the solvent was removed via a rotary evaporator. The residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent to yield 1.24 g (74%) of 25 as a yellow solid.

Workup

stirringThe resulting mixture was then stirred at room temperature overnight
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over Na2SO4
customthe solvent was removed via a rotary evaporator
customThe residue was purified by chromatography on silica gel using 7:3 hexane/ethyl acetate as the eluent

Sources & evidence

ORD record: ord-25e07eadc45e419c8c81cb2a002db935
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700616B2

Reaction notes

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