Water → HCID 14809498, compound

HRID 649323Notes

Reaction equation

HRID 649323 reaction equation
[H-].[Na+].Br[CH2:4][CH2:5][CH2:6][Cl:7].C(OCC)(=O)C.O.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24]1([S:36][CH3:37])[C:29](=[O:30])[N:28]([CH3:31])[C:27]2[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=2[S:25]1>CN(C)C=O>[Cl:7][CH2:6][CH2:5][CH2:4][O:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=1[C:24]1([S:36][CH3:37])[C:29](=[O:30])[N:28]([CH3:31])[C:27]2[CH:32]=[CH:33][CH:34]=[CH:35][C:26]=2[S:25]1

Participants

7

Reactant 5

HCID 962WaterHCID 80061-Bromo-3-chloropropaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14809494HCID 14809494, compound

Product 1

HCID 14809498HCID 14809498, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 60% sodium hydride (0.5 g) in dimethylformamide (10 ml), 3,4-dihydro-2-(2-hydroxy-5-methoxyphenyl)-4-methyl-2-methylthio-3-oxo-2H-1,4-benzothiazine (3.5 g, compound No. 8) dissolved in dimethylformamide (5 ml) is added under nitrogen atmosphere and ice-cooling, and the mixture is stirred for 10 minutes at room temperature. 1-Bromo-3-chloropropane (1.9 g) is added to the reaction mixture, and the mixture is stirred for 1 hour at 50°-60° C. The mixture is poured into a mixture of ethyl acetate and water. The organic layer is washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The separated crystals are collected by filtration to give 4.0 g (93.4%) of the titled compound.

Workup

  1. additionis added under nitrogen atmosphere
  2. temperatureice-cooling
  3. stirringthe mixture is stirred for 1 hour at 50°-60° C
  4. washThe organic layer is washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. filtrationThe separated crystals are collected by filtration

Sources & evidence

ORD record
ord-c6fcb699b3f44607a6fbae79d18938f3
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

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