Ethyl orthoformate → HCID 44203112, compound

HRID 2201561Notes

Reaction equation

HRID 2201561 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[CH:18](OCC)(OCC)OCC>>[Br:17][C:14]1[CH:13]=[C:3]2[C:2](=[CH:16][CH:15]=1)[N:1]=[CH:18][N:6]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:4]2=[O:5]

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 12233737HCID 12233737, compound

Product 1

HCID 44203112HCID 44203112, compoundYield 50%

Conditions

Temperature
130 °C

Procedure

A mixture of 2-amino-5-bromo-N-phenylbenzamide (2.82 g, 9.7 mmol) and triethyl orthoformate (20 mL) was stirred at 130° C. for 15 h. The reaction mixture was cooled to RT and petroleum ether was added. After filtration, the filtrate was extracted with ethyl acetate (100 mL*3), the combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified with silica gel column chromatograph (PE:EtOAc=5:1) to give 6-bromo-3-phenylquinazolin-4(3H)-one (1.5 g, yield: 50%) as white solid. 1H-NMR (CDCl3, 400 MHz) δ 8.50 (d, J=2.4 Hz, 1H), 8.13 (s, 1H), 7.87˜7.90 (m, 1H), 7.65 (d, J=8.8 Hz, 1H), 7.55˜7.58 (m, 2H), 7.51˜7.53 (m, 1H), 7.41˜7.43 (m, 2H). MS (M+H)+:301/303.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationAfter filtration
  3. extractionthe filtrate was extracted with ethyl acetate (100 mL*3)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel column chromatograph (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-e092ff6208ae403bb119a477a8208670
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

Loading…