Ethyl thiooxamate → Ethyl 9-bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-D]thiazole-2-carboxylate

HRID 707797Notes

Reaction equation

HRID 707797 reaction equation
Br[CH:2]1[CH2:8][CH2:7][O:6][C:5]2[CH:9]=[CH:10][C:11]([Br: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]([Br:13])=[CH:12][C:4]=3[C:3]=2[N:22]=1)=[O:17])[CH3:20]

Participants

4

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 579004584,7-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Product 1

HCID 67050521Ethyl 9-bromo-4,5-dihydrobenzo[2,3]oxepino[4,5-D]thiazole-2-carboxylateYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 4,7-dibromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one (3.4 g, 11 mmol) and ethyl thioamidooxalate (4.2 g, 32 mmol) was added ethanol (81 mL) and heated at reflux (at 80° C.) for 4 days. The reaction mixture was cooled to room temperature and cooled in an ice bath. The precipitate was collected by filtration to give 9-Bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene-2-carboxylic acid ethyl ester (2.59 g, 69%). LC/MS (ESI+): m/z 355 (M+H).

Workup

  1. temperatureheated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. temperaturecooled in an ice bath
  4. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-aa365b8f6ef049639521e0f31d6bedcd
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

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