Furfural → HCID 178478186, compound

HRID 1486565Notes

Reaction equation

HRID 1486565 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH2:15])[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH:16](=O)[C:17]1[O:21][CH:20]=[CH:19][CH:18]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:14]=[C:13]([NH:15][CH2:16][C:17]3[O:21][CH:20]=[CH:19][CH:18]=3)[NH:12][N:11]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 7362FurfuralHCID 4311764Sodium borohydrideHCID 727146143-Amino-5-(3,5-dichloroanilino)-s-triazole

Product 1

HCID 178478186HCID 178478186, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (70 mg, 287 μmol) and furfural (85.1 mg, 886 μmol) in MeOH (3 ml) was stirred at room temperature for 3 days. The resulting suspension was filtered to collect the solid. The solid was re-suspended in MeOH (5 ml), NaBH4 (65.1 mg, 1.72 mmol) was added and the reaction was stirred for 1 hour. The solvent was removed, and the reaction mixture was redissolved in DCM and washed with water (2×4 ml), dried over MgSO4 and concentrated to give a solid. Trituration with DCM/Hexanes afforded a white solid as desired product (50.5 mg, 54% yield). MS +m/z: 324 (M+H)+

Workup

  1. filtrationThe resulting suspension was filtered
  2. customto collect the solid
  3. customThe solvent was removed
  4. dissolutionthe reaction mixture was redissolved in DCM
  5. washwashed with water (2×4 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customto give a solid

Sources & evidence

ORD record
ord-84671450badb41faac4e7ff2b37c2f04
Source dataset
uspto-grants-2016_08
Patent number
US09428469B2

Reaction notes

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