Methyl iodide → HCID 19369481, compound

HRID 1418873Notes

Reaction equation

HRID 1418873 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][CH:31]=1)[CH2:16][NH:17][C:18]1[C:27]2[S:26][CH2:25][C:24](=[O:28])[NH:23][C:22]=2[CH:21]=[CH:20][CH:19]=1.CI.[C:34]([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].CN(C=O)C>[CH3:34][N:23]1[C:22]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:17][CH2:16][C:15]3[CH:29]=[CH:30][CH:31]=[C:13]([O:12][CH2:11][C:2]4[CH:3]=[CH:4][C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[N:1]=4)[CH:14]=3)[C:27]=2[S:26][CH2:25][C:24]1=[O:28]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 19369493HCID 19369493, compound

Product 1

HCID 19369481HCID 19369481, compoundYield 57.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

After a mixture of 1.690 g (3.95 mmol) of 8-[3-(2-quinolinylmethoxy)benzylamino]-3,4-dihydro-2H-1,4-benzothiazin-3-one obtained in Example 95, 0.673 g (4.74 mmol) of CH3I, 1.311 g (9.5 mmol) of K2CO3, 0.129 g (0.4 mmol) of (n-Bu)4NBr and 50 ml of DMF was stirred at room temperature for 3 days, the solvent was distilled off under reduced pressure. Water was added to the residue, followed by extraction with CHCl3. The extract was washed with water, dried over MgSO4 and then concentrated. The residue was subjected to chromatography on a silica gel column. Subsequent to elution with CHCl3, recrystallization was conducted from an acetone-n-hexane mixed solvent, whereby 1.000 g of the title compound was obtained (yield: 57.3%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionWater was added to the residue
  3. extractionfollowed by extraction with CHCl3
  4. washThe extract was washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. washSubsequent to elution
  8. customwith CHCl3, recrystallization

Sources & evidence

ORD record
ord-21a864262b7b4ace9d2785168026cdfe
Source dataset
uspto-grants-1999_03
Patent number
US05885987

Reaction notes

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