Water → HCID 66879628, compound

HRID 1893554Notes

Reaction equation

HRID 1893554 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][C:3]=1[N+:13]([O-])=O.[H-].[Na+].[CH3:18]I.O>CN(C)C=O>[NH2:13][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[CH3:1])[N:9]([CH3:18])[C:8](=[O:12])[CH2:7][CH2:6]2

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66881586HCID 66881586, compound

Product 1

HCID 66879628HCID 66879628, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (3.14 g, 15.2 mmol) obtained in step A was dissolved in N,N-dimethylformamide (30 ml), 60% sodium hydride (730 mg, 18.2 mmol) was added under ice-cooling with stirring, and thereafter the mixture was stirred at room temperature for 30 min. The reaction mixture was ice-cooled again, methyl iodide (1.9 ml, 30.4 mmol) was added with stirring, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water, and the precipitated solid was collected by filtration, washed with water, and dried under reduced pressure to give a bistered solid. Using this solid and according to the method of Reference Example 116, step B, the title compound (1.76 g, yield 61%) was obtained as a pale-bistered solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 30 min
  3. temperaturecooled again
  4. stirringwith stirring
  5. stirringthe mixture was stirred at room temperature for 1 hr
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with water
  8. customdried under reduced pressure
  9. customto give a bistered solid

Sources & evidence

ORD record
ord-0f895cc325c140d6bb0df571cc5e46c1
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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