Pyridine → HCID 178489100, compound

HRID 1637584Notes

Reaction equation

HRID 1637584 reaction equation
[C:1](Cl)(=[O:9])[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N[C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[NH:14][N:13]=1.[N:25]1C=CC=CC=1>>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[NH:14][N:13]=[C:12]([C:1]([O:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)=[O:9])[C:16]=2[NH2:25])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 27564693-Amino-5-(4-methoxyphenyl)pyrazole

Product 1

HCID 178489100HCID 178489100, compound

Procedure

Phenyl chlorocarbonate (0.87 ml) was added to a solution of 3-amino-5-(4-methoxyphenyl)pyrazole (1.19 g) in pyridine (10 ml), and the mixture was stirred at room temperature for 6 hours. The reaction solution was partitioned between ethyl acetate (50 ml) and water (30 ml), and the organic layer was washed with 1 N hydrochloric acid (50 ml×2), saturated aqueous sodium bicarbonate (50 ml) and saturated brine (50 ml) and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled away. The resulting residue was crystallized from ethyl acetate/hexane to obtain the title compound (0.95 g) as pale yellow crystals (melting point: 286-291° C.).

Workup

  1. customThe reaction solution was partitioned between ethyl acetate (50 ml) and water (30 ml)
  2. washthe organic layer was washed with 1 N hydrochloric acid (50 ml×2), saturated aqueous sodium bicarbonate (50 ml) and saturated brine (50 ml)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThen, the solvent was distilled away
  5. customThe resulting residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b8e560bfb8a944f396898e061bb4240d
Source dataset
uspto-grants-2000_03
Patent number
US06043246

Reaction notes

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