Methyl iodide → 6-(3,6-dichloro-pyridazine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

HRID 469335Notes

Reaction equation

HRID 469335 reaction equation
[H-].[Na+].[Cl:3][C:4]1[N:5]=[N:6][C:7]([Cl:23])=[CH:8][C:9]=1[C:10]([C:12]1[CH:21]=[C:20]([CH3:22])[C:15]2[NH:16][C:17](=[O:19])[O:18][C:14]=2[CH:13]=1)=[O:11].I[CH3:25]>CN(C=O)C>[Cl:3][C:4]1[N:5]=[N:6][C:7]([Cl:23])=[CH:8][C:9]=1[C:10]([C:12]1[CH:21]=[C:20]([CH3:22])[C:15]2[N:16]([CH3:25])[C:17](=[O:19])[O:18][C:14]=2[CH:13]=1)=[O:11]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 581811846-(3,6-dichloro-pyridazine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811216-(3,6-dichloro-pyridazine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

85 mg (2.1 mmol) sodium hydride (55%, suspension in mineral oil) were added to 0.65 g (2.0 mmol) 6-(3.6-dichloro-pyridazine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10 mL DMF while cooling with ice. The reaction mixture was stirred for 20 min. Then 0.19 mL (3.1 mmol) iodomethane were added while cooling with ice and the mixture was stirred for 2 h at RT. The reaction mixture was mixed with ice water, the precipitate formed was suction filtered and dried.

Workup

  1. temperaturewhile cooling with ice
  2. temperaturewhile cooling with ice
  3. stirringthe mixture was stirred for 2 h at RT
  4. customthe precipitate formed
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-70b76502fbb94a3d98d2be5a1b61b37f
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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