Sodium hydride → Ethyl 2-[4-(5-fluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetate

HRID 1655892Notes

Reaction equation

HRID 1655892 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][CH:3]1[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].Br[CH2:21][C:22]1[S:23][C:24]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:25]=2[N:26]=1>CN(C)C=O>[F:31][C:28]1[CH:29]=[CH:30][C:24]2[S:23][C:22]([CH2:21][N:7]3[C:6]4[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=4[S:4][CH:3]([CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:2]3=[O:1])=[N:26][C:25]=2[CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2778792Ethyl 2-(3-oxo-3,4-dihydro-2h-1,4-benzothiazin-2-yl)acetateHCID 144586272-(Bromomethyl)-5-fluorobenzo[d]thiazole

Product 1

HCID 9909828Ethyl 2-[4-(5-fluorobenzothiazol-2-yl)methyl-3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl]acetateYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Under ice cooling, 1.01 g of ethyl 2-(3,4-dihydro-3-oxo-2H-1,4-benzothiazin-2-yl)acetate was added to a suspension of 176 mg of sodium hydride (60% in mineral oil) in 7 ml of N,N-dimethylformamide. The mixture was stirred for 30 minutes. After a solution of 1.08 g of 2-bromomethyl-5-fluorobenzothiazole in 3 ml of N,N-dimethylformamide was added dropwise to the mixture, the mixture was stirred at room temperature overnight. Thereafter the reaction mixture was poured onto ice water, and then extracted with ethyl acetate. 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 residue was purified by silica gel chromatography to give 1.11 g of the title compound. The structural formula and physical data of this compound are shown in Table 7.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. additionThereafter the reaction mixture was poured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialAfter the drying of the organic layer over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting oily residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-193138008d6f4a69839a680afdf36c34
Source dataset
uspto-grants-1993_10
Patent number
US05252571

Reaction notes

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