Ethyl thiooxamate → HCID 58203736, compound

HRID 1849442Notes

Reaction equation

HRID 1849442 reaction equation
Br[CH:2]1[CH2:8][CH2:7][O:6][C:5]2[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:4]=2[C:3]1=O.[C:15]([NH2:22])(=[S:21])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)C>[CH2:19]([O:18][C:16]([C:15]1[S:21][C:2]2[CH2:8][CH2:7][O:6][C:5]3[CH:9]=[CH:10][C:11]([F:13])=[CH:12][C:4]=3[C:3]=2[N:22]=1)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 58204120HCID 58204120, compound

Product 1

HCID 58203736HCID 58203736, compoundYield 62.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolved 4-bromo-7-fluoro-3,4-dihydrobenzo[b]oxepin-5(2H)-one (1.06 g, 4.09 mmol) in ethanol (100 mL) and added Ethyl Thioamidooxalate (1.09 g, 8.18 mmol). Heated to reflux with a vigreux condensation column attached. Allowed to stir a reflux overnight and confirmed complete reaction by LCMS. Concentrated in vacuo and purified by flash chromatography using ethyl acetate/heptanes (0 to 10% over 60 minutes) to give 0.75 g (62% yield) of 9-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester

Workup

  1. temperatureHeated
  2. temperatureto reflux with a vigreux condensation column
  3. customreaction by LCMS
  4. concentrationConcentrated in vacuo
  5. custompurified by flash chromatography
  6. customethyl acetate/heptanes (0 to 10% over 60 minutes)

Sources & evidence

ORD record
ord-225e823836904e7886c2197094636f19
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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