Diphenylamine → HCID 68280128, compound

HRID 1771075Notes

Reaction equation

[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>CN(C=O)C>[C:10]1([N:9]([CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=2)[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

NaH (0.220 g, 5.54 mmol) was dissolved in anhydrous DMF (2 mL) under argon and cooled to 0° C. To it was added diphenylamine (0.0.750 g, 4.43 mmol) dissolved in anhydrous DMF (2 mL). The reaction was stirred for 15 min at 0° C. followed by the addition of methyl 4-(bromomethyl)benzoate (1.02 g, 4.43 mmol) in anhydrous DMF (2 mL). The reaction was stirred for 2 h at 60° C. and then quenched by the addition of H2O (20 mL). The organic products were extracted with EtOAc (3×30 mL), washed with H2O (2×30 mL), brine (15 mL), dried with Na2SO4, filtered and concentrated in vacuo. The title compound was purified using automated column chromatography method 1 (0.746 g, 53%). 1H NMR (400 MHz, CDCl3): δ 8.00 (d, J=8.2 Hz, 2H), 7.45 (d, J=7.7 Hz, 2H), 7.27 (m, 4H), 7.07 (d, J=7.9 Hz, 4H), 6.98 (t, J=7.3 Hz, 2H), 5.06 (s, 2H), 3.92 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 166.9, 147.8, 144.8, 130.0, 129.4, 128.9, 126.5, 121.7, 120.7, 56.3, 52.0. ESI-LRMS: [M+H]+=318 m/z.

Workup

stirringThe reaction was stirred for 2 h at 60° C.
customquenched by the addition of H2O (20 mL)
extractionThe organic products were extracted with EtOAc (3×30 mL)
washwashed with H2O (2×30 mL), brine (15 mL)
dry with materialdried with Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe title compound was purified

Sources & evidence

ORD record: ord-73d70cfaee564405a03a56d0ae715fb0
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249087B2

Reaction notes

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