Water → HCID 68870935, compound

HRID 1986346Notes

Reaction equation

[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=1.Cl[C:15]1[CH:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:18]([N+:28]([O-:30])=[O:29])=[CH:17][N:16]=1.O>CN(C=O)C>[N+:28]([C:18]1[C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:20][C:15]([O:3][C:4]2[CH:5]=[C:6]([NH:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:8][CH:9]=2)=[N:16][CH:17]=1)([O-:30])=[O:29]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium hydride (60% dispersion in oil, 16.24 g, 406 mmol) was suspended in DMF (800 mL) and solid N-(3-hydroxyphenyl)acetamide (61.0 g, 406 mol) was added portionwise over 1 h (warming and frothing occurs). After the final addition the product from Step 4 (101.2 g, 406 mmol) was added as a solid, portionwise, over 10 min and the resulting mixture was heated to 60° C. overnight. Water (800 mL) was carefully added dropwise to the still warm reaction mixture over 1 h to give a fine yellow precipitate. The mixture was then cooled to 0° C., filtered and the resulting solid was washed with cold H2O and hexane to give the title compound (143.3 g, 97%) as a yellow solid. 1H NMR (400 MHz, DMSO-D6) δ ppm 10.06 (s, 1H), 9.80 (s, 1H), 8.91 (s, 1H), 7.44-7.49 (m, 3H), 7.37 (dd, 2H, 1.26 Hz, 8.6 Hz), 7.29-7.33 (m, 3H), 6.76-6.80 (m, 1H), 6.22 (s, 1H), 2.04 (s, 3H). MS (ES+) m/e 365 [M+H]+.

Workup

temperature(warming and frothing occurs)
additionwas added as a solid
customto give a fine yellow precipitate
temperatureThe mixture was then cooled to 0° C.
filtrationfiltered
washthe resulting solid was washed with cold H2O and hexane

Sources & evidence

ORD record: ord-db62a4bbc51a4f26be764e32e5500c1a
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

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