Methyl iodide → HCID 58181155, compound

HRID 469316Notes

Reaction equation

HRID 469316 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([C:16]2[CH:25]=[C:24]([CH3:26])[C:19]3[NH:20][C:21](=[O:23])[O:22][C:18]=3[CH:17]=2)=[O:15])[CH:11]=[CH:10][N:9]=1.CI>C1COCC1.CCOC(C)=O>[Cl:7][C:8]1[CH:13]=[C:12]([C:14]([C:16]2[CH:25]=[C:24]([CH3:26])[C:19]3[N:20]([CH3:1])[C:21](=[O:23])[O:22][C:18]=3[CH:17]=2)=[O:15])[CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 58181177HCID 58181177, compound

Product 1

HCID 58181155HCID 58181155, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

220 mg (1.94 mmol) potassium-tert-butoxide were added to 500 mg (1.73 mmol) 6-(2-chloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10.0 mL THF and the mixture was stirred for 30 min at RT. Then 0.220 mL (3.46 mmol) methyl iodide were added and the mixture was stirred overnight at RT. The reaction mixture was diluted with EtOAc and washed several times with saturated sodium chloride solution. The organic phase was dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was triturated with DIPE and suction filtered.

Workup

  1. stirringthe mixture was stirred overnight at RT
  2. washwashed several times with saturated sodium chloride solution
  3. customThe organic phase was dried on magnesium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe residue was triturated with DIPE and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-ba58168412e6441099d9fabe3ad91151
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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