N-bromobutanimide → HCID 178518920, compound

HRID 1400084Notes

Reaction equation

HRID 1400084 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[N:8]=[N:7][C:6]([OH:9])=[CH:5][CH:4]=1.[Br:12]N1C(=O)CCC1=O>C(O)(=O)C.C(#N)C.ClCCl>[Br:12][C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:10])[F:11])[N:8]=[N:7][C:6]=1[OH:9]

Participants

6

Reactant 2

HCID 67184N-bromobutanimideHCID 178516045HCID 178516045, compound

Product 1

HCID 178518920HCID 178518920, compoundYield 95.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-trifluoromethyl-pyridazin-3-ol (9.0 g, 54.9 mmol) (D3) and N-bromosuccinimide (12.7 g, 71.4 mmol) in a mixture of acetic acid (15 ml) and acetonitrile (350 ml) was stirred at 60° C. for 6 h. and at room temperature for a further 16 h. After this period, the reaction mixture was diluted with dichloromethane and extracted with a 10% solution of sodium thiosulfite. The organic layer was separated, dried (MgSO4) and the solvent evaporated in vacuo to yield D4 (12.7 g, 95%) as a yellow solid. C5H2BrF3N2O requires 243; Found 244 (MH+).

Workup

  1. waitAfter this period
  2. extractionextracted with a 10% solution of sodium thiosulfite
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-286afd6652fd4a058b19543ad7d291ee
Source dataset
uspto-grants-2014_12
Patent number
US08906921B2

Reaction notes

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