Water → 4-Cyano-4-(2-isopropyl-7-methoxybenzoxazol-4-yl)cyclohexanone

HRID 842602Notes

Reaction equation

[C:1]([C:3]1([C:14]2[C:19]3[N:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[O:22][C:18]=3[C:17]([O:26][CH3:27])=[CH:16][CH:15]=2)[CH2:8][CH:7](C(OC)=O)[C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2].[Na+].[Cl-].O>CS(C)=O>[C:1]([C:3]1([C:14]2[C:19]3[N:20]=[C:21]([CH:23]([CH3:25])[CH3:24])[O:22][C:18]=3[C:17]([O:26][CH3:27])=[CH:16][CH:15]=2)[CH2:8][CH2:7][C:6](=[O:13])[CH2:5][CH2:4]1)#[N:2]

Participants

Conditions

Temperature: 140 °C

Procedure

0.69 g (1.86 mmol) of methyl 5-cyano-5-(2-isopropyl-7-methoxybenzoxazol-4-yl)-2-oxocyclohexanecarboxylate (starting compound A8) is dissolved in 16 ml of DMSO, a solution of 0.73 g of NaCl in 2 ml of dist. water is added and the mixture is stirred at 140° C. for 8.5 h. After cooling the reaction mixture, it is diluted with 80 ml of dist. water and extracted with ethyl acetate, and the organic phase is separated off, dried over magnesium sulfate and concentrated to dryness in vacuo. After chromatography, the title compound (0.45 g) is obtained as a colorless solid. TLC, silica gel (glass plates), petroleum ether/ethyl acetate (7:3), Rf=0.56, m.p. 118° C.

Workup

temperatureAfter cooling the reaction mixture, it
additionis diluted with 80 ml of dist
extractionwater and extracted with ethyl acetate
customthe organic phase is separated off
dry with materialdried over magnesium sulfate
concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record: ord-bfd69fbee8c64b78bb92bf7726c308e3
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06376485B1

Reaction notes

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