Triethylamine → HCID 136409062, compound

HRID 1750162Notes

Reaction equation

HRID 1750162 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.C(N(CC)CC)C.[C:14]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)#[N:15].[C:24]([O:30][CH2:31][CH:32]=[CH2:33])(=[O:29])[CH2:25][C:26]([CH3:28])=O>CC(O)C>[CH2:31]([O:30][C:24]([C:25]1[CH:20]([C:19]2[CH:22]=[CH:23][C:16]([C:14]#[N:15])=[CH:17][CH:18]=2)[N:3]2[N:4]=[CH:5][N:6]=[C:2]2[NH:1][C:26]=1[CH3:28])=[O:29])[CH:32]=[CH2:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 660424-CyanobenzaldehydeHCID 70701Allyl acetoacetateHCID 178418311HCID 178418311, compound

Product 1

HCID 136409062HCID 136409062, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

3-amino-1,2,4-triazole (1.28 mg, 15.24 mmol) and triethylamine (2.2 ml, 15.25 mmol) were heated in IPA (30 ml) at 90° C. until most of the solid had dissolved. 4-Cyanobenzaldehyde (2.0 g, 15.27 mmol) and allyl acetoacetate (2.17 g, 15.28 mmol) were added and the reaction was heated at 90° C. overnight. The volatiles were evaporated and the residue was partitioned between ethyl acetate and water. Some solid material was filtered off and the ethyl acetate layer was separated, washed with brine, dried (Na2SO4) and the volume reduced. The solid which precipitated was filtered, washed with ethyl acetate and combined with the solid obtained earlier. The pale yellow product was dried in vacuo at 40° C.

Workup

  1. dissolutionhad dissolved
  2. customThe volatiles were evaporated
  3. customthe residue was partitioned between ethyl acetate and water
  4. filtrationSome solid material was filtered off
  5. customthe ethyl acetate layer was separated
  6. washwashed with brine
  7. dry with materialdried (Na2SO4)
  8. customThe solid which precipitated
  9. filtrationwas filtered
  10. washwashed with ethyl acetate
  11. customobtained earlier
  12. customThe pale yellow product was dried in vacuo at 40° C.

Sources & evidence

ORD record
ord-b5d0aae1f6004d3f859af4b34afb7ba2
Source dataset
uspto-grants-2015_10
Patent number
US09156844B2

Reaction notes

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