1-Bromo-3-chloropropane → HCID 20143107, compound

HRID 649320Notes

Reaction equation

HRID 649320 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[CH:13]1[C:18](=[O:19])[N:17]([CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=2[S:14]1.Br[CH2:26][CH2:27][CH2:28][Cl:29].C(OCC)(=O)C>CN(C)C=O.O>[Cl:29][CH2:28][CH2:27][CH2:26][C:13]1([C:6]2[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=2[O:4][CH3:3])[C:18](=[O:19])[N:17]([CH3:20])[C:16]2[CH:21]=[CH:22][CH:23]=[CH:24][C:15]=2[S:14]1

Participants

7

Reactant 4

HCID 80061-Bromo-3-chloropropaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 14244693HCID 14244693, compound

Product 1

HCID 20143107HCID 20143107, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a stirred suspension of 60% sodium hydride (0.7 g) in anhydrous dimethylformamide (10 ml), 3,4-dihydro-2-(2,5-dimethoxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine (5.0 g) dissolved in anhydrous dimethylformamide (15 ml) is added under nitrogen atmosphere and ice-cooling, and the mixture is stirred for 20 minutes at room temperature. 1-Bromo-3-chloropropane (3.0 g) dissolved in dimethylformamide (5 ml) is added to a reaction mixture, and the mixture is stirred for 1.5 hours at 50° 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 residue is purified by silica gel column chromatography to give 5.4 g (86.9%) of the titled compound as an oily form.

Workup

  1. additionis added under nitrogen atmosphere
  2. temperatureice-cooling
  3. additionis added to a reaction mixture
  4. stirringthe mixture is stirred for 1.5 hours at 50° C
  5. washThe organic layer is washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-854bdfeef73e4b7d85fccfbc4c4f3ee1
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

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