2,1,3-Benzoxadiazol-4(5H)-one, 5-bromo-6,7-dihydro- → 4,5-Dihydro[1,3]thiazolo[4,5-e][2,1,3]benzoxadiazol-7-amine

HRID 255080Notes

Reaction equation

HRID 255080 reaction equation
Br[CH:2]1[C:10](=O)[C:6]2=[N:7][O:8][N:9]=[C:5]2[CH2:4][CH2:3]1.[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[N:7]1[O:8][N:9]=[C:5]2[CH2:4][CH2:3][C:2]3[S:14][C:13]([NH2:15])=[N:12][C:10]=3[C:6]=12

Participants

4

Reactant 2

HCID 5729162,1,3-Benzoxadiazol-4(5H)-one, 5-bromo-6,7-dihydro-HCID 2723790Thiourea

Product 1

HCID 8993834,5-Dihydro[1,3]thiazolo[4,5-e][2,1,3]benzoxadiazol-7-amineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution commercially available 5-bromo-6,7-dihydro-5H-benzo[1,2,5]oxadiazol-4-one (1.1 g, 5.1 mmol) in absolute ethanol (60 mL) was added thiourea. The mixture was stirred at 60° C. overnight and then concentrated. The residue was triturated in hexanes and then collected by filtration to afford 1.3 g (90%) of the title compound MS (ESI+) m/z 195 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated in hexanes
  3. filtrationcollected by filtration

Sources & evidence

ORD record
ord-225c454b4e234d29a6c3b14babb44205
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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