Methyl iodide → 6-(3,4-Dihydro-4-methanesulfonyl-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydro-2-methylpyridazin-3-one

HRID 1090308Notes

Reaction equation

HRID 1090308 reaction equation
[CH3:1][S:2]([N:5]1[C:10]2[CH:11]=[C:12]([C:15]3[CH2:16][CH2:17][C:18](=[O:21])[NH:19][N:20]=3)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)(=[O:4])=[O:3].[H-].[Na+].[CH3:24]I>CN(C)C=O>[CH3:1][S:2]([N:5]1[C:10]2[CH:11]=[C:12]([C:15]3[CH2:16][CH2:17][C:18](=[O:21])[N:19]([CH3:24])[N:20]=3)[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][CH2:6]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14230055HCID 14230055, compound

Product 1

HCID 142300566-(3,4-Dihydro-4-methanesulfonyl-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydro-2-methylpyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-(3,4-Dihydro-4-methanesulfonyl-1,4(2H)-benzoxazin-6-yl)-2,3,4,5-tetrahydropyridazin-3-one (3 g) was suspended in 50 ml of dimethylformamide and one equivalent of 60% sodium hydride in oil was added. When gas evolution ceased, one equivalent of methyl iodide was added and the mixture allowed to stand for 1.5 hours followed by one hour at 40° C. The mixture was cooled and then poured into 200 ml of ice water, giving a precipitate that was collected by filtration, washed with water and recrystallized from ethanol. The material was further purified by chromatography on silica gel eluted with 1:1 EtOAc:Et2O yielding 0.97 g of the title product, mp 162°-165° C.

Workup

  1. waitfollowed by one hour at 40° C
  2. temperatureThe mixture was cooled
  3. customgiving a precipitate that
  4. filtrationwas collected by filtration
  5. washwashed with water
  6. customrecrystallized from ethanol
  7. customThe material was further purified by chromatography on silica gel
  8. washeluted with 1:1 EtOAc

Sources & evidence

ORD record
ord-9ffc30cde6cf43a196b9ddaf95fce00b
Source dataset
uspto-grants-1992_01
Patent number
US05081242

Reaction notes

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