Tetrahydrofuran → HCID 86596461, compound

HRID 499400Notes

Reaction equation

HRID 499400 reaction equation
O[CH2:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][C:11]3[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=3[C:13](=[O:15])[N:14]=2)[CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.C[S:28](Cl)(=[O:30])=[O:29].[O:32]1[CH2:36]CCC1>O>[O:15]=[C:13]1[C:12]2[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=2[S:10][C:9]([C:7]2[N:8]=[C:3]([CH2:2][S:28]([O:32][CH3:36])(=[O:30])=[O:29])[CH:4]=[CH:5][CH:6]=2)=[N:14]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22939400HCID 22939400, compound

Product 1

HCID 86596461HCID 86596461, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(6-Hydroxymethyl-2-pyridyl)-4H-1,3-benzothiazine-4-one (0.54 g, 2.0 mmol) and triethylamine (0.31 ml, 2.2 mmol) were dissolved in tetrahydrofuran (30 ml). Methanesulfonyl chloride (0.16 ml, 2.1 mmol) was added to the mixture while the mixture was stirred under ice cooling condition. The reaction mixture was stirred at room temperature for 3 hrs, diluted with water and extracted with chloroform. The extract was washed with water and dried. The solvent was evaporated under reduced pressure. The obtained crystals were recrystallized from ethanol to give the titled compound (0.64 g, 92%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hrs
  2. extractionextracted with chloroform
  3. washThe extract was washed with water
  4. customdried
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-759f962bcf6e4a299fd50c86d759e8e4
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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