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

HRID 469320Notes

Reaction equation

HRID 469320 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([C:17]2[CH:26]=[C:25]([CH3:27])[C:20]3[NH:21][C:22](=[O:24])[O:23][C:19]=3[CH:18]=2)=[O:16])[CH:12]=[C:11]([Cl:28])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:30]>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:15]([C:17]2[CH:26]=[C:25]([CH3:27])[C:20]3[N:21]([CH3:30])[C:22](=[O:24])[O:23][C:19]=3[CH:18]=2)=[O:16])[CH:12]=[C:11]([Cl:28])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 581811156-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one

Product 1

HCID 581811066-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-3,4-dimethyl-3H-benzoxazol-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere and while cooling with ice 220 mg (5.06 mmol) sodium hydride (55%, suspension in mineral oil) were added to 2.00 g (5.07 mmol) 6-(2-benzyloxy-6-chloro-pyridine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one in 10 mL DMF. The reaction mixture was stirred for 30 min at RT. Then 0.312 mL (5.06 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. The residue was stirred 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. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. stirringThe residue was stirred with diethyl ether, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-f2c114a7a7fe4764b59b69caa2526c50
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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