Methyl iodide → HCID 86651865, compound

HRID 469347Notes

Reaction equation

HRID 469347 reaction equation
[H-].[Na+].Cl[C:4]1C=C(C(C2C=C(C)C3NC(=O)OC=3C=2)=O)C(C)=CN=1.[Cl:24][C:25]1[C:30]([CH3:31])=[C:29]([C:32]([C:34]2[CH:43]=[C:42]([CH3:44])[C:37]3[NH:38][C:39](=[O:41])[O:40][C:36]=3[CH:35]=2)=[O:33])[CH:28]=[CH:27][N:26]=1.IC>CN(C=O)C>[Cl:24][C:25]1[C:30]([CH3:31])=[C:29]([C:32]([C:34]2[CH:43]=[C:42]([CH3:44])[C:37]3[N:38]([CH3:4])[C:39](=[O:41])[O:40][C:36]=3[CH:35]=2)=[O:33])[CH:28]=[CH:27][N:26]=1

Participants

6

Reactant 4

HCID 6328Methyl iodide2×HCID 24758Sodium hydrideHCID 58181174HCID 58181174, compoundHCID 86651864HCID 86651864, compound

Product 1

HCID 86651865HCID 86651865, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.10 g (2.2 mmol) sodium hydride (55%, suspension in mineral oil) were added to 0.61 g (2.0 mmol) 6-(2-chloro-5-methyl-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in admixture with 6-(2-chloro-3-methyl-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 5 mL DMF at RT. The reaction mixture was stirred for 30 min at RT. Then 0.17 mL (2.6 mmol) iodomethane were added and the mixture was stirred for 1 h at RT. Then a further 0.1 mL iodomethane were added and the mixture was stirred further at RT. Ice water was added to the reaction mixture and the precipitate formed was suction filtered. The residue was purified by flash chromatography. The fractions containing the product were combined, evaporated down, triturated with diethyl ether, suction filtered and dried. The product was obtained in admixture with 6-(2-chloro-3-methyl-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one and reacted further as such.

Workup

  1. stirringthe mixture was stirred for 1 h at RT
  2. stirringthe mixture was stirred further at RT
  3. customthe precipitate formed
  4. filtrationfiltered
  5. customThe residue was purified by flash chromatography
  6. additionThe fractions containing the product
  7. customevaporated down
  8. customtriturated with diethyl ether, suction
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-a1b655b5e8a44896a2ea2c70535fdfea
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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