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

HRID 469318Notes

Reaction equation

HRID 469318 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:19]=[C:18]([CH3:20])[C:13]3[NH:14][C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[O:9])[CH:5]=[C:4]([Cl:21])[N:3]=1.[H-].[Na+].I[CH3:25]>CN(C=O)C>[Cl:21][C:4]1[CH:5]=[C:6]([C:8]([C:10]2[CH:19]=[C:18]([CH3:20])[C:13]3[N:14]([CH3:25])[C:15](=[O:17])[O:16][C:12]=3[CH:11]=2)=[O:9])[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 581812126-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811136-(2,6-dichloro-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere 2.30 g (7.12 mmol) 6-(2,6-dichloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10 mL DMF were combined at 0° C. with 310 mg (7.10 mmol) sodium hydride (55%, suspension in mineral oil). The reaction mixture was stirred for 30 min at RT. Then 0.44 mL (7.10 mmol) iodomethane were added and the mixture was stirred overnight at RT. The reaction mixture was poured onto water and the precipitated product was suction filtered, washed with water and dried.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. additionThe reaction mixture was poured onto water
  3. filtrationfiltered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-7ebadc50ff094270bcb5d9fab9c9b3be
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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