Sodium hydride → 4-Chloro-6-methyl-11h-5-oxa-10-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

HRID 2425086Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5](=[O:24])[C:6]1[CH:11]=[C:10]([CH3:12])[C:9](Br)=[C:8]([S:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[C:17]=2[OH:23])[CH:7]=1>CN(C=O)C>[CH3:3][O:4][C:5]([C:6]1[CH:11]=[C:10]([CH3:12])[C:9]2[O:23][C:17]3[C:18]([Cl:22])=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14][C:8]=2[CH:7]=1)=[O:24]

Participants

Conditions

Temperature: 80 °C

Procedure

Sodium hydride (1.65 g, 0.068 mol) was added portionwise to a solution of compound of Example 15a (23 g, 0.057 mol) in DMF (600 mL) and stirred at 80° C. for 10 h. The solvent was removed, and chloroform (300 mL) was added. The organic layer was washed with 10% HCl (2×80 mL), followed by water (100 mL), and brine and dried over anhydrous sodium sulphate. The solvent was removed and the crude product obtained was purified by column chromatography (silica gel, ethyl acetate/pet ether) to obtain the title compound. Yield: 9 g, (49%); 1H NMR (CDCl3, 300 MHz): δ 2.50 (s, 3H, CH3), 3.91 (s, 3H, OCH3), 4.21 (s, 2H, CH2), 7.05 (m, 2H, Ar), 7.28 (d, 1H, Ar), 7.60 (d, 2H, Ar); MS: m/e (EI) 320 (M+).

Workup

customThe solvent was removed
additionchloroform (300 mL) was added
washThe organic layer was washed with 10% HCl (2×80 mL)
dry with materialdried over anhydrous sodium sulphate
customThe solvent was removed
customthe crude product obtained
customwas purified by column chromatography (silica gel, ethyl acetate/pet ether)

Sources & evidence

ORD record: ord-0024f9a9ce30498eb36d14b2b9b94075
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964631B2

Reaction notes

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