Dimethylamine → HCID 22267875, compound

HRID 488793Notes

Reaction equation

HRID 488793 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([C:16]([OH:18])=O)=[N:7][N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:9]=1)=[O:4].[C:19](N1C=CN=C1)([N:21]1C=CN=[CH:22]1)=O.CNC>CN(C=O)C>[CH3:19][N:21]([CH3:22])[C:16]([C:6]1[C:5]([C:3]([O:2][CH3:1])=[O:4])=[N:9][N:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:7]=1)=[O:18]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22267595HCID 22267595, compound

Product 1

HCID 22267875HCID 22267875, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

A solution of 5-methoxycarbonyl-2-phenyl-2H-1,2,3-triazole-4-carboxylic acid (0.203 g, 0.82 mmol) in dry DMF (3 mL) at 23° C. was treated with carbonyldiimidazole (0.146 g, 0.90 mmol). The resulting mixture was stirred for 1.5 h at 23° C., cooled to 0° C. and treated with dimethylamine (2.0 M, in THF, 2.05 mL, 4.10 mmol). The resulting mixture was allowed to warm to 23° C. over 16 h and concentrated in vacuo. The residue was partitioned between water and EtOAc. The aqueous layer was extracted with an additional portion of EtOAc. The combined organic extracts were washed with HCl (1 M), brine, NaHCO3 (sat. aq. sol.) and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by filtering it through a silica gel plug (EtOAc-hexanes 50:50) to afford 0.201 g (89%) of methyl 5-(N,N-dimethylcarbamoyl)-2-phenyl-2H-1,2,3-triazole-4-carboxylate.

Workup

  1. temperaturecooled to 0° C.
  2. temperatureto warm to 23° C. over 16 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was partitioned between water and EtOAc
  5. extractionThe aqueous layer was extracted with an additional portion of EtOAc
  6. washThe combined organic extracts were washed with HCl (1 M), brine, NaHCO3 (sat. aq. sol.) and brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified
  10. filtrationby filtering it through a silica gel plug (EtOAc-hexanes 50:50)

Sources & evidence

ORD record
ord-ab6b6c9bc4f949fa89b3e9193cd94ff1
Source dataset
uspto-grants-2005_12
Patent number
US06974813B2

Reaction notes

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