Triethylamine → HCID 54060579, compound

HRID 1741148Notes

Reaction equation

HRID 1741148 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]([NH:15][NH2:16])=[O:14].C(N(CC)CC)C.[C:24](C1NC=CN=1)(C1NC=CN=1)=[O:25]>O1CCCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[CH:12][C:13]1[O:14][C:24](=[O:25])[NH:16][N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 70290411HCID 70290411, compound

Product 1

HCID 54060579HCID 54060579, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of 3-naphthalen-2-yl-acrylic acid hydrazide (1.0 g, 4.71 mmol, prepared as described in example 5) and triethylamine (0.64 g, 6.28 mmol) in dry tetrahydrofuran (15 ml) was added carbonyl diimidazole (1.02 g, 6.28 mmol) at 0° C. The reaction mixture was stirred at room temperature for 1 h. The resulting reaction mixture was evaporated in vacuo and to the residue was added water (25 ml). The precipitate was filtered off and washed with water (2×10 ml) and diethyl ether (2×10 ml) and recrystallised from ethyl acetate (100 ml) affording after drying in vacuo at 50° C. 0.5 g (45%) of the title compound as a solid.

Workup

  1. customThe resulting reaction mixture
  2. customwas evaporated in vacuo and to the residue
  3. additionwas added water (25 ml)
  4. filtrationThe precipitate was filtered off
  5. washwashed with water (2×10 ml) and diethyl ether (2×10 ml)
  6. customrecrystallised from ethyl acetate (100 ml)
  7. customaffording
  8. customafter drying in vacuo at 50° C

Sources & evidence

ORD record
ord-352bb733c01d49e8adeeabdb848f0cd6
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

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