Hydrochloric Acid → HCID 12477809, compound

HRID 2424940Notes

Reaction equation

HRID 2424940 reaction equation
[H-].[Na+].Cl[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[NH:15][C:16](=[O:18])[CH3:17])=[O:6].Cl>COCCOC>[C:16]([N:15]1[C:8]2[C:7](=[CH:12][CH:11]=[C:10]([O:13][CH3:14])[CH:9]=2)[C:5](=[O:6])[CH2:4]1)(=[O:18])[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 12477793HCID 12477793, compound

Product 1

HCID 12477809HCID 12477809, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of NaH (60% dispersion in mineral oil, 3.97 g, 99.3 mmol) in DME (75 mL) was added an ice-cold solution of N-[2-(chloroacetyl)-5-methoxyphenyl]acetamide (12.00 g, 49.7 mmol) (Example 11) in DME (165 mL) at 0° C. The mixture was stirred under argon for 15 minutes, then 2 N HCl (75 mL) solution was added slowly. The mixture was extracted with dichloromethane. The combined organic layers were dried over MgSO4 and concentrated to yield a solid. The crude material was purified on silica gel eluting with EtOAc/hexane (1:1) and then EtOAc to give a reddish solid (7.87 g, 77%) with minor impurities: LC/MS m/z 206 (M+H)+; 1H NMR (400 MHz, DMSO-d6) 7.94 (d, 1H), 7.59 (d, 1H), 6.80 (dd, 1H), 4.51 (s, 2H), 3.85 (s, 3H), 2.24 (s, 3H).

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. concentrationconcentrated
  4. customto yield a solid
  5. customThe crude material was purified on silica gel eluting with EtOAc/hexane (1:1)

Sources & evidence

ORD record
ord-52adf8bad6fb4226b392489a48afbe2b
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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