Water → [4-(4-Benzoylamino-2-nitrophenoxy)-phenyl]carbamic acid tert-butyl ester

HRID 605265Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].[C:20]([NH:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].[OH-].[K+].O>CS(C)=O>[C:23]([O:22][C:20](=[O:21])[NH:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:2]2[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:16])[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][C:3]=2[N+:17]([O-:19])=[O:18])=[CH:32][CH:33]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(4-fluoro-3-nitrophenyl)benzamide (1.00 g, 3.8 mmol), N-Boc-4-hydroxyaniline (0.83 g, 3.8 mmol) and 85% KOH (0.51 g, 7.7 mmol) in DMSO (20 mL) was heated at 80° C. for 1 hour, and then poured into H2O (100 ml) under stirring. The resulting oily crystal was extracted with EtOAc. The extract was washed with H2O (3 times) and brine, dried over MgSO4, filtered and concentrated under vacuum giving the crude title compound, which was purified by washing with i-Pr2O to give the desired compound as yellow crystals (1.59 g, 92%).

Workup

extractionThe resulting oily crystal was extracted with EtOAc
washThe extract was washed with H2O (3 times) and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum
customgiving the crude title compound, which
customwas purified
washby washing with i-Pr2O

Sources & evidence

ORD record: ord-0346ac4040c94a799838694124054c87
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07910595B2

Reaction notes

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