Hydrazine → HCID 58504781, compound

HRID 2367371Notes

Reaction equation

HRID 2367371 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([F:10])[C:5]([C:6]#[N:7])=[C:4](F)[CH:3]=1.[NH2:12][NH2:13].CCN(C(C)C)C(C)C>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:6]([NH2:7])=[N:12][NH:13]2)=[C:8]([F:10])[CH:9]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 27569164-Bromo-2,6-difluorobenzonitrile

Product 1

HCID 58504781HCID 58504781, compoundYield 410.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

Five batches of the below reaction were run in sequence in a microwave reactor: To a 5-mL microwave vial was added 4-bromo-2,6-difluorobenzonitrile (3 g, 13.76 mmol), hydrazine (0.864 mL, 27.5 mmol), Hunig's base (4.81 mL, 27.5 mmol) and ethanol (10 mL). The vial was capped and stirred for 10 minutes at 150° C. in a microwave reactor. The reaction mixture was cooled (ice-water bath) and a yellow precipitate formed. The yellow precipitates were collected, combined and the solids were washed with cold ethanol to yield pale yellow rods of the title compound (13.0 g). LC-MS (ES) m/z=230 and 232 (1:1 intensity) [M+H]+.

Workup

  1. customFive batches of the below reaction
  2. customwere run in sequence in a microwave reactor
  3. customThe vial was capped
  4. customa yellow precipitate formed
  5. customThe yellow precipitates
  6. customwere collected
  7. washthe solids were washed with cold ethanol

Sources & evidence

ORD record
ord-831549215c384c47b1dfecc80ddc3762
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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