Methyl iodide → 6-(2-chloro-6-methoxy-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

HRID 469330Notes

Reaction equation

HRID 469330 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[NH:16][C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:7]=[C:6]([O:23][CH3:24])[N:5]=1.I[CH3:26]>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[C:8]([C:10]([C:12]2[CH:21]=[C:20]([CH3:22])[C:15]3[N:16]([CH3:26])[C:17](=[O:19])[O:18][C:14]=3[CH:13]=2)=[O:11])[CH:7]=[C:6]([O:23][CH3:24])[N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 581811586-(2-chloro-6-methoxy-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811676-(2-chloro-6-methoxy-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under a nitrogen atmosphere 0.13 g (2.9 mmol) sodium hydride (55%, suspension in mineral oil) were added 0.90 g (2.8 mmol) 6-(2-chloro-6-methoxy-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10 mL DMF at RT. The reaction mixture was stirred for 30 min at RT. Then 0.18 mL (5.0 mmol) iodomethane in 1 mL DMF were added dropwise and the mixture was stirred overnight at RT. The reaction mixture was poured onto water and the precipitate formed was suction filtered and washed with water. The residue was extracted with diethyl ether, suction filtered and dried.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. additionThe reaction mixture was poured onto water
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washwashed with water
  6. extractionThe residue was extracted with diethyl ether, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-9d24e9c8bdd5440c84e00be90e7268c6
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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