Water → HCID 67954591, compound

HRID 1846390Notes

Reaction equation

HRID 1846390 reaction equation
[Na].[F:2][C:3]1[C:4]([CH3:18])=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[NH:11])[CH:6]=[CH:7][CH:8]=1.C([O:21][CH:22]=[C:23]([C:29](OCC)=O)[C:24]([O:26]CC)=[O:25])C.O.C(=O)(O)[O-].[Na+]>C(#N)C>[F:2][C:3]1[C:4]([CH3:18])=[C:5]([N:9]2[C:22](=[O:21])[C:23]([C:24]([OH:26])=[O:25])=[CH:29][N:11]=[C:10]2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 6871Diethyl (ethoxymethylene)malonateHCID 516892Sodium BicarbonateHCID 178429746HCID 178429746, compound2×

Product 1

HCID 67954591HCID 67954591, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of N-(3-fluoro-2-methylphenyl)benzenecarboximidamide sodium salt (1:1) (i.e. the product from Example 5, Step A) (51.0 g, 200 mmol) in acetonitrile (300 mL) was added diethyl ethoxymethylenemalonate (44.04 g, 200 mmol). The reaction was stirred at room temperature for 30 min followed by the addition of water (3.6 mL, 200 mmol). The reaction was then stirred for another 30 min Water (100 mL) was added to the residue, followed by a saturated solution of sodium bicarbonate (300 mL), and the mixture was extracted with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid until the pH was 1-2, and the mixture was extracted with dichloromethane. The organic layer was dried (MgSO4) and concentrated under reduced pressure to provide a solid, which was washed with diethyl ether and dried under reduced pressure to afford the title product as a off-white solid (18 g).

Workup

  1. additionwas added to the residue
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto provide a solid, which
  7. washwas washed with diethyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-95de3333d57943418ed85d6939311149
Source dataset
uspto-grants-2015_02
Patent number
US08952024B2

Reaction notes

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