Hydrogen Bromide → HCID 11164006, compound

HRID 362647Notes

Reaction equation

HRID 362647 reaction equation
N[C:2]1[N:6]([C:7]2[C:11]([Cl:12])=[C:10]([O:13][CH:14]([F:16])[F:15])[N:9]([CH3:17])[N:8]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19].N([O-])=O.[Na+].[BrH:24]>O>[Br:24][C:2]1[N:6]([C:7]2[C:11]([Cl:12])=[C:10]([O:13][CH:14]([F:16])[F:15])[N:9]([CH3:17])[N:8]=2)[N:5]=[CH:4][C:3]=1[C:18]#[N:19]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 15346385HCID 15346385, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11164006HCID 11164006, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-6 °C

Procedure

5.68 g (19.7 mmol) 5-Amino-1-(4-chloro-5-difluoromethoxy-1-methyl-3-pyrazolyl)-4-pyrazolecarbonitrile was dissolved in 66.3 ml hydrobromic acid (47%) and the mixture cooled to -6° C. Under a nitrogen atmosphere, 2.36 g (34.2 mmol) sodium nitrite in 5.9 ml water was added dropwise. The mixture was stirred for 15 minutes at this temperature and heated to room temperature. 200 ml water was then added and the mixture extracted 4 times with methylene chloride. The organic phase was washed with saturated aqueous sodium hydrogen carbonate, dried over magnesium sulfate and concentrated.

Workup

  1. temperatureheated to room temperature
  2. extractionthe mixture extracted 4 times with methylene chloride
  3. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-076bb33b0b0e4c0caed08561052d68ca
Source dataset
uspto-grants-1999_02
Patent number
US05869686

Reaction notes

Loading…