Benzyl Bromide → HCID 86747277, compound

HRID 1655893Notes

Reaction equation

HRID 1655893 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4]/[C:3]/1=[CH:12]\[C:13]([O:15][CH3:16])=[O:14].[H-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[S:4]/[C:3](=[CH:12]\[C:13]([O:15][CH3:16])=[O:14])/[C:2]1=[O:1])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 5476764NSC266486

Product 1

HCID 86747277HCID 86747277, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Methyl (Z)-2-(3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-ylidene)acetate (940 mg) was dissolved in 8 ml of N,N-dimethylformamide, and the solution was added dropwise to a suspension of sodium hydride (60% in oil, 192 mg) in 2 ml of N,N-dimethylformamide. The mixture was stirred for 30 minutes. To the mixture was added dropwise a solution of 752 mg of benzyl bromide in 2 ml of N,N-dimethylformamide. The stirring was continued for an hour under ice-cooling, the reaction mixture was poured onto ice water, and extracted with ethyl acetate. Then, the ethyl acetate layer was washed with water. After the drying of the organic layer over anhydrous magnesium sulfate, the solvent was distilled off. The resulting oily matter was solidified in isopropyl etherhexane to give 1.04 g of methyl (Z)-2-(4-benzyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-ylidene)acetate as yellow powder. The structural formula and physical data of this compound are shown in Table 14.

Workup

  1. waitThe stirring was continued for an hour under ice-
  2. temperaturecooling
  3. additionthe reaction mixture was poured onto ice water
  4. extractionextracted with ethyl acetate
  5. washThen, the ethyl acetate layer was washed with water
  6. dry with materialAfter the drying of the organic layer over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-2641a4857c0345b5a5f5e49b2c3fd012
Source dataset
uspto-grants-1993_10
Patent number
US05252571

Reaction notes

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