Sodium Hydroxide → HCID 19911844, compound

HRID 1534007Notes

Reaction equation

[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[S:17][C:16]([C:18]([O:20]C)=[O:19])=[C:15]([S:22](=[O:29])(=[O:28])[NH:23][C:24]([F:27])([F:26])[F:25])[CH:14]=1.[OH-].[Na+]>CO>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[S:17][C:16]([C:18]([OH:20])=[O:19])=[C:15]([S:22](=[O:28])(=[O:29])[NH:23][C:24]([F:25])([F:27])[F:26])[CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

38.0 g (0.085 mol) of methyl 5-(2-quinolinylmethoxy)-3-(1,1,1-trifluoromethylsulphamoyl)-2-thiophenecarboxylate are dissolved in 350 ml of methanol and about 100 ml of 2N sodium hydroxide solution are added. The reaction mixture is heated under reflux and with stirring for 7 hours. The reaction solution is concentrated to 20% of its volume and diluted with 500 ml of water. The aqueous phase is extracted four times with a total of 500 ml of ether. The aqueous phase is cooled to 0° C. with stirring and acidified with 0.5N hydrochloric acid. The product precipitated in this way is filtered off with suction, digested twice with 50 ml of ice-cold ether each time and dried at 60° C./1 mbar.

Workup

temperatureThe reaction mixture is heated
temperatureunder reflux
concentrationThe reaction solution is concentrated to 20% of its volume
additiondiluted with 500 ml of water
extractionThe aqueous phase is extracted four times with a total of 500 ml of ether
stirringwith stirring
customThe product precipitated in this way
filtrationis filtered off with suction
customdried at 60° C./1 mbar

Sources & evidence

ORD record: ord-82d112fa72d446fcbb5afd67ef0512a1
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05086180

Reaction notes

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