Formamide → HCID 9928576, compound

HRID 429329Notes

Reaction equation

HRID 429329 reaction equation
C[O-].[Na+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([C:26](OCC)=O)=[N:12]2)=[CH:7][C:6]=1[CH3:31].C([NH2:34])=O>>[F:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]3[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=3)=[CH:14][C:13]([C:26]#[N:34])=[N:12]2)=[CH:7][C:6]=1[CH3:31]

Participants

4

Reactant 3

HCID 713FormamideHCID 10942334Sodium MethoxideHCID 18355406HCID 18355406, compound

Product 1

HCID 9928576HCID 9928576, compound

Conditions

Temperature
110 °C

Procedure

A mixture of sodium methoxide (169 mg) and ethyl 1-(4-fluoro-3-methylphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carboxylate (420 mg) in formamide (5 ml) was warmed at 110° C. for 30 minutes. The reaction mixture was poured into ice-water (50 ml) and the precipitate was collected by filtration, and washed with water and dried in vacuo. To an ice-cooled solution of POCl3 (0.23 ml) in dimethylformamide (3 ml) was added the residue by small portions under nitrogen atmosphere. After 2 hours, the mixture was poured into water (50 ml) and stirred for 30 minutes. The resulting precipitates were collected by filtration and washed with water and dried in vacuo. The resulting residue was purified by column chromatography on silica gel using chloroform and was recrystallized from ethanol to afford 1-(4-fluoro-3-methylphenyl)-5-[4-(methylsulfonyl)phenyl]pyrazole-3-carbonitrile (297 mg).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. customdried in vacuo
  4. temperatureTo an ice-cooled solution of POCl3 (0.23 ml) in dimethylformamide (3 ml)
  5. additionwas added the residue by small portions under nitrogen atmosphere
  6. additionthe mixture was poured into water (50 ml)
  7. customThe resulting precipitates
  8. filtrationwere collected by filtration
  9. washwashed with water
  10. customdried in vacuo
  11. customThe resulting residue was purified by column chromatography on silica gel
  12. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-f68293be808342d99adb248d02e2c737
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Reaction notes

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