Hydrochloric Acid → HCID 67258482, compound

HRID 907953Notes

Reaction equation

HRID 907953 reaction equation
[O:1]=[C:2]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH2:8][O:9][C:10]2=[O:15])=[O:4].[H-].[Na+].Cl[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1.Cl>CN(C=O)C.C(OCC)(=O)C.O>[CH3:33][O:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:5]([C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[CH2:8][O:9][C:10]3=[O:15])[C:3](=[O:4])[C:2](=[O:1])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:27][CH:28]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 67386784HCID 67386784, compound

Product 1

HCID 67258482HCID 67258482, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-oxo-N-(1-oxo-1,3-dihydroisobenzofuran-4-yl)-2-phenylacetamide (5 g, 11.7 mmol) in DMF (48 mL) was added NaH (0.78 g, 19.5 mmol). The solution was stirring at room temperature for 1.5 hr, followed by the addition of 1-(chloromethyl)-4-methoxy-benzene (2.8 mL). After stirred at 30° C. overnight, the resulting mixture was added water and adjusted to pH=3-4 with 0.5 N aq. HCl. Then ethyl acetate was added, concentrated and filtered, the filtrate was washed by ethyl acetate, the combine ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, concentrated, and purified by flash chromatography on silica gel to obtain the desired compound (4.7 g, yield 66%). LC-MS (ESI) m/z: 402 (M+1)+. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 3.73 (s, 3H), 4.83-5.17 (m, 4H), 6.89-6.91 (d, J=8.8 Hz, 2H), 7.18-7.20 (m, 2H), 7.24-7.26 (m, 1H), 7.38-7.42 (t, 1H), 7.52-7.56 (m, 2H), 7.69-7.71 (m, 1H), 7.75-7.81 (m, 3H).

Workup

  1. stirringAfter stirred at 30° C. overnight
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washthe filtrate was washed by ethyl acetate
  5. washthe combine ethyl acetate layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0bbb3ceb358445558c422f6e6cdf0638
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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