Sodium hydride → 2-Benzo[1,3]dioxol-5-ylmethyl-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl ester

HRID 1449536Notes

Reaction equation

HRID 1449536 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][S:7](=[O:17])(=[O:16])[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4].[H-].[Na+].[CH2:20]1[O:30][C:29]2[CH:28]=[CH:27][C:24]([CH2:25]Cl)=[CH:23][C:22]=2[O:21]1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([CH2:25][C:24]2[CH:27]=[CH:28][C:29]3[O:30][CH2:20][O:21][C:22]=3[CH:23]=2)[S:7](=[O:17])(=[O:16])[C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]=1[OH:11])=[O:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 887131,3-Benzodioxole, 5-(chloromethyl)-HCID 54676531methyl 4-hydroxy-2H-1,2-benzothiazine-3-carboxylate 1,1-dioxide

Product 1

HCID 700589382-Benzo[1,3]dioxol-5-ylmethyl-4-hydroxy-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2]thiazine-3-carboxylic acid methyl esterYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-hydroxy-1,1-dioxo-1,2-dihydro-1λ6 -benzo[e][1,2]thiazine-3-carboxylic acid methyl ester (1.48 g, 5.84 mmol) in DMF (10 mL) was added sodium hydride (0.257 g, 60%, 6.4 mmol) and the mixture stirred for 5 minutes. 3,4-methylenedioxybenzyl chloride (2.2 g, 50 wt. % in dichloromethane, 6.4 mmol) was added and the mixture stirred at room temperature for 18 hours. Diluted with ethyl acetate (100 mL), washed with water (2×80 mL), brine (80 mL), dried over magnesium sulfate, removed solvent in vacuo, and crystallized from ethyl acetate/heptane to give the title compound (1.63 g, 72%);

Workup

  1. stirringthe mixture stirred at room temperature for 18 hours
  2. washwashed with water (2×80 mL), brine (80 mL)
  3. dry with materialdried over magnesium sulfate
  4. customremoved solvent in vacuo
  5. customcrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-3a40f597e94e4c44b377109078a03840
Source dataset
uspto-grants-1997_02
Patent number
US05599811

Reaction notes

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