Water → HCID 20438213, compound

HRID 1979698Notes

Reaction equation

HRID 1979698 reaction equation
C([O:4][CH:5]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:6]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]=O)[CH:17]=2)[N:8]([CH3:24])[N:7]=1)(=O)C.[CH2:31]([NH2:37])[C:32]1[O:36][CH:35]=[CH:34][CH:33]=1.[BH4-].[Na+].O>C(O)C>[O:36]1[CH:35]=[CH:34][CH:33]=[C:32]1[CH2:31][NH:37][CH2:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[O:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]1[N:8]([CH3:24])[N:7]=[C:6]([CH:5]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[OH:4])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3438FurfurylamineHCID 4311764Sodium borohydrideHCID 54030473HCID 54030473, compound

Product 1

HCID 20438213HCID 20438213, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 5-[[3-(3-formylphenoxy)propyl]amino]-1-methyl-α-phenyl-1H-1,2,4-triazole-3-methanol acetate (ester) (1.0 g) and furfurylamine (5 ml) in ethanol (30 ml) was stirred at 21° for 1.5 h before a suspension of sodium borohydride (1.3 g) in ethanol (10 ml) was added and stirring was continued for a further 16 h at 21°. Water (20 ml) was added, the mixture concentrated to remove ethanol and the aqueous residue extracted with 4-methylpentan-2-one. The extract was dried and evaporated to give an oil. Excess furfurylamine was removed in vacuo and the residue was dissolved in 2N hydrochloric acid, the acidic layer washed with ethyl acetate, basified (pH 9) with sodium carbonate, and extracted with 4-methylpentan-2-one. The extract was washed with water, dried and evaporated to give a brown gum (0.65 g) which was chromatographed on silica (Merck No. 7729) using System B as eluent to give the title compound (0.5 g) as a pale orange gum.

Workup

  1. additionwas added
  2. concentrationthe mixture concentrated
  3. customto remove ethanol
  4. extractionthe aqueous residue extracted with 4-methylpentan-2-one
  5. customThe extract was dried
  6. customevaporated
  7. customto give an oil
  8. customExcess furfurylamine was removed in vacuo
  9. dissolutionthe residue was dissolved in 2N hydrochloric acid
  10. washthe acidic layer washed with ethyl acetate
  11. extractionextracted with 4-methylpentan-2-one
  12. washThe extract was washed with water
  13. customdried
  14. customevaporated

Sources & evidence

ORD record
ord-0899a06f3ae74710acec75da51d4c9ba
Source dataset
uspto-grants-1984_11
Patent number
US04482552

Reaction notes

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