Dimethylformamide → HCID 21223477, compound

HRID 1584107Notes

Reaction equation

HRID 1584107 reaction equation
C([Li])CCC.CC(NC(C)C)C.[C:13]1([CH2:19][CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C)[CH:28]=[O:29]>CCCCCC.O1CCCC1>[C:13]1([CH2:19][CH2:20][N:21]2[C:25]([CH:28]=[O:29])=[N:24][CH:23]=[N:22]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 3696281-(2-phenylethyl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 21223477HCID 21223477, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of butyllithium in hexane (119 ml) was added dropwise at -70° C. under nitrogen to a solution of N-(1-methylethyl)-2-propanamine (26.7 ml) in tetrahydrofuran (280 ml) and the mixture was stirred for 30 minutes. 1-(2-phenylethyl)-1,2,4-triazole (0.173 mol) in tetrahydrofuran (20 ml) was added and the mixture was stirred at -70° C. for 1 hour. N,N-dimethylformamide (17.4 ml) was added dropwise and the mixture was stirred at -70° C. for 1 hour and then at room temperarure for 2 hours. The mixture was poured into ice water and extracted with 1,1'-oxybisethane. The organic layer was dried (MgSO4), filtered off and evaporated. The residue (11.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 99/1/0.1) (35-70 μm). The pure fractions were collected and evaporated, yielding 7g (40%) of 2-(2-phenylethyl)-2H-1,2,4-triazole-3-carboxaldehyde (interm. 1).

Workup

  1. stirringthe mixture was stirred at -70° C. for 1 hour
  2. stirringthe mixture was stirred at -70° C. for 1 hour
  3. waitat room temperarure for 2 hours
  4. extractionextracted with 1,1'-oxybisethane
  5. dry with materialThe organic layer was dried (MgSO4)
  6. filtrationfiltered off
  7. customevaporated
  8. customThe residue (11.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 99/1/0.1) (35-70 μm)
  9. customThe pure fractions were collected
  10. customevaporated

Sources & evidence

ORD record
ord-f5cd19229c444904ae78f8bf2a7e99e4
Source dataset
uspto-grants-1999_08
Patent number
US05932569

Reaction notes

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