Ethyl thiooxamate → HCID 86693056, compound

HRID 575022Notes

Reaction equation

HRID 575022 reaction equation
Br[CH:2]1[CH2:8][CH2:7][O:6][C:5]2[CH:9]=[C:10]([F:14])[C:11]([Br:13])=[CH:12][C:4]=2[C:3]1=O.[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])(=[S:18])[NH2:17]>C(O)C.CN1C(=O)CCC1>[CH2:22]([O:21][C:19]([C:16]1[S:18][C:2]2[CH2:8][CH2:7][O:6][C:5]3[CH:9]=[C:10]([F:14])[C:11]([Br:13])=[CH:12][C:4]=3[C:3]=2[N:17]=1)=[O:20])[CH3:23]

Participants

5

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 86693054HCID 86693054, compound

Product 1

HCID 86693056HCID 86693056, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 13387N-methyl-2-pyrrolidoneCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Into a 20-L 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed 4,7-Dibromo-8-fluoro-3,4-dihydro-2H-benzo[b]oxepin-5-one (1400 g, 4.14 mol, 1.00 equiv), NMP (0 mg), and ethyl carbamothioylformate (554 g, 4.16 mol, 1.00 equiv). The resulting solution was stirred at 80° C. for 3 h, cooled to 25° C. and diluted with 6 L of ethanol. The solids were collected by filtration, washed with 3×1 L of ethanol and dried to afford 390 g (25%) of 9-Bromo-8-fluoro-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester

Workup

  1. customInto a 20-L 4-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperaturecooled to 25° C.
  4. filtrationThe solids were collected by filtration
  5. washwashed with 3×1 L of ethanol
  6. customdried

Sources & evidence

ORD record
ord-8a70fb4f3c924f5b81f34abaf7568e16
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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