Potassium Carbonate → HCID 67040780, compound

HRID 605352Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[C:15]([O:19][C:20](=[O:29])[NH:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)([CH3:18])([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([O:28][C:25]2[CH:24]=[CH:23][C:22]([NH:21][C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:29])=[CH:27][CH:26]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 4-chloro-3-nitrobenzoic acid methyl ester (15.0 g, 68 mmol), (4-hydroxy-phenyl)-carbamic acid tert-butyl ester (14.7 g, 68 mmol) and K2CO3 (18.9 g, 136 mmol) in DMF (300 mL) was heated at 110° C. for 1 hour under N2, cooled to room temperature, and then poured into ice-H2O (1200 mL) under stirring. The aqueous mixture was extracted with AcOEt (600 mL). The extract was washed with H2O (3 times) and brine, dried over MgSO4, and evaporated to give pale brown crystal, which was purified by washing with i-Pr2O and dried at 40° C. overnight under reduced pressure to give the title compound as pale yellow crystal (18.5 g, 70%).

Workup

temperaturecooled to room temperature
extractionThe aqueous mixture was extracted with AcOEt (600 mL)
washThe extract was washed with H2O (3 times) and brine
dry with materialdried over MgSO4
customevaporated
customto give pale brown crystal, which
customwas purified
washby washing with i-Pr2O
customdried at 40° C. overnight under reduced pressure

Sources & evidence

ORD record: ord-6a0416d2d829439faf290d2ded266777
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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