Potassium Carbonate → HCID 86727412, compound

HRID 519047Notes

Reaction equation

HRID 519047 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].Br[CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[S:8][CH2:9][C:10](=[O:12])[N:11]([CH:16]([CH3:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79040Ethyl 2-bromopropionateHCID 41823566-Nitro-2H-benzo[b][1,4]thiazin-3(4H)-one

Product 1

HCID 86727412HCID 86727412, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-nitro-2H-benzo[b][1,4]thiazin-3(4H)-one (0.512 g, 2.436 mmol), ethyl 2-bromopropanoate (0.573 g, 3.17 mmol) and K2CO3 (1.01 g, 7.31 mmol) in acetone (40 mL) was heated at reflux for 16 h. After cooling to ambient temperature, the mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by column chromatography on silica gel (eluting with 9% EtOAc in petroleum ether) to give ethyl 2-(6-nitro-3-oxo-2H-benzo[b][1,4]thiazin-4(3H)-yl)propanoate (0.376 g, 50%). TLC (eluting with 20% EtOAc/PE) Rf=0.6.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (eluting with 9% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-0df583ad44e94cab8d6dceac8e5fc4f5
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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