Epichlorohydrin → HCID 20143001, compound

HRID 649318Notes

Reaction equation

HRID 649318 reaction equation
[H-].[Na+].[C:3]([C:5]1([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[C:10](=[O:11])[N:9]([CH3:12])[C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[S:6]1)#[N:4].[CH2:24]([CH:26]1[O:28][CH2:27]1)Cl.C(OCC)(=O)C>CN(C)C=O.O>[C:3]([C:5]1([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH:26]3[O:28][CH2:27]3)=[CH:21][CH:22]=2)[C:10](=[O:11])[N:9]([CH3:12])[C:8]2[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=2[S:6]1)#[N:4]

Participants

7

Reactant 4

HCID 7835EpichlorohydrinHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 20143022HCID 20143022, compound

Product 1

HCID 20143001HCID 20143001, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 60% sodium hydride (0.7 g) in anhydrous dimethylformamide (5 ml), 2-cyano-3,4-dihydro-2-(4-hydroxyphenyl)-4-methyl-3-oxo-2H-1,4-benzothiazine (5.0 g, compound No. 10) dissolved in anhydrous dimethylformamide (15 ml) is added under nitrogen atmosphere and ice-cooling, and the mixture is stirred for 7 minutes at room temperature. Epichlorohydrin(2.6 ml) is added to the reaction mixture, and the mixture is stirred for 1 hour at 65°-75° 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 3.2 g (54.5%) of the titled compound.

Workup

  1. additionis added under nitrogen atmosphere
  2. temperatureice-cooling
  3. stirringthe mixture is stirred for 1 hour at 65°-75° 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. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8ea1ab673834c6fb6bf881459115fbb
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

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