Hydrogen Bromide → HCID 11164006, compound

HRID 1080394Notes

Reaction equation

HRID 1080394 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-5f0df82d7eff4c8595990658b77c93c0
Source dataset
uspto-grants-1996_12
Patent number
US05580986

Reaction notes

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