Hydrochloric Acid → HCID 19366016, compound

HRID 850080Notes

Reaction equation

HRID 850080 reaction equation
N[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:9]([C:19]#[N:20])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22].[ClH:26].N([O-])=O.[Na+]>[Cu]Cl.C(OCC)(=O)C>[Cl:26][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[C:9]([C:19]#[N:20])[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 19366045HCID 19366045, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19366016HCID 19366016, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution (15 ml) of ethyl 5-amino-1-(3-cyano-4-neopentyloxyphenyl)pyrazole-4-carboxylate (2.09 g) obtained in Example 31 in con. hydrochloric acid was added an aqueous solution (4 ml) of sodium nitrite (0.62 g) with stirring under ice-cooling. To this diazonium salt solution was gradually added copper (I) chloride (1.49 g) under ice-cooling. After the dropwise addition, the reaction mixture was heated at 60° C. for 1 hour. After the completion of the reaction, the reaction mix was enacted with ethyl acetate, washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was applied to silica gel column chromatography to give 0.74 g of ethyl 5chloro-1-(3-cyano-4-neopentyloxyphenyl)pyrazole-4-carboxylate, melting point 90-92° C.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. additionAfter the dropwise addition
  4. customAfter the completion of the reaction
  5. additionthe reaction mix
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3696403e60b64cb092ec6912bc87c5a2
Source dataset
uspto-grants-2000_01
Patent number
US06015829

Reaction notes

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