Tetrahydrofuran → HCID 178482488, compound

HRID 544281Notes

Reaction equation

HRID 544281 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH:23]([CH3:24])[CH2:22][C:21]([NH:25][CH:26]=O)=[N:20]2)=[CH:15][CH:14]=1.[OH-].[Na+]>O>[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[CH:23]([CH3:24])[CH2:22][C:21]([NH:25][CH3:26])=[N:20]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 15580713HCID 15580713, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 178482488HCID 178482488, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a stirred solution of 250 ml. of freshly distilled tetrahydrofuran under nitrogen is added cautiously 3.3 g. of lithium aluminum hydride, then 3.3 g. of N-[1-(p-chlorophenyl)-5-methyl-2-pyrazolin-3-yl]formamide is added and the mixture is refluxed under nitrogen for 4 hours. The reaction mixture is cooled. Then with stirring, 3.3 ml. of water is cautiously added dropwise, followed by 3.3 ml. of 15% aqueous sodium hydroxide solution and 10.0 ml. of water. The mixture is filtered and the residue is washed with ether. The combined filtrate and wash is evaporated to dryness giving a gum which solidifies. The solid is collected, washed with hexane and dried. The product of the Example is recrystallized from dichloromethane-hexane to give 2.3 g. of white crystals, m.p. 102°-103° C.

Workup

  1. temperaturethe mixture is refluxed under nitrogen for 4 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe mixture is filtered
  4. washthe residue is washed with ether
  5. washThe combined filtrate and wash
  6. customis evaporated to dryness
  7. customgiving a gum which
  8. customThe solid is collected
  9. washwashed with hexane
  10. customdried
  11. customto give 2.3 g

Sources & evidence

ORD record
ord-78b6e17a332e4116b6e721c3023fadfd
Source dataset
uspto-grants-1984_05
Patent number
US04448973

Reaction notes

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