Triethylamine → HCID 57659740, compound

HRID 1897561Notes

Reaction equation

HRID 1897561 reaction equation
[C:1]([O:6][CH2:7][CH3:8])(=S)[C:2]([NH2:4])=O.F[B-](F)(F)F.C([O+:16](CC)CC)C.[CH2:21]([NH:28][NH:29][C:30](=O)[C:31]([CH3:34])([CH3:33])[CH3:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[C:31]([C:30]1[N:4]=[C:2]([C:1]([O:6][CH2:7][CH3:8])=[O:16])[N:28]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:29]=1)([CH3:34])([CH3:32])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9375PivhydrazineHCID 2723982Triethyloxonium tetrafluoroborateHCID 216137632-ethoxy-2-thioxoAcetamide

Product 1

HCID 57659740HCID 57659740, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl thiooxamate (0.27 g, 2.0 mmol) and triethyloxonium tetrafluoroborate (0.40 g, 2.1 mmol) in CH2Cl2 (25 mL) was stirred at room temperature 2 h. The reaction was cooled in an ice bath, and a solution of N′-benzylpivalohydrazide (0.41 g, 2.0 mmol) and triethylamine (0.28 mL, 2.0 mmol) in CH2Cl2 (10 mL) was slowly added. The cooling bath was removed, and the reaction was heated to reflux for 90 min. The solvent was removed under vacuum, and the residue was purified by silica gel chromatography (0%-25% EtOAc-hexanes) to obtain ethyl 5-tert-butyl-2-benzyl-2H-1,2,4-triazole-3-carboxylate (0.23 g, 40% yield). 1H NMR (400 MHz, CDCl3) δ 7.34-7.28 (m, 5H), 5.73 (s, 2H), 4.43 (q, J=7.1 Hz, 2H), 1.40 (s, 9H), 1.38 (t, J=7.7 Hz, 3H) ppm. LC/MS: m/z 288.2 (M+H)+ at 3.51 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. customThe cooling bath was removed
  3. temperaturethe reaction was heated
  4. temperatureto reflux for 90 min
  5. customThe solvent was removed under vacuum
  6. customthe residue was purified by silica gel chromatography (0%-25% EtOAc-hexanes)

Sources & evidence

ORD record
ord-f934ef5d2c294e68be9cc75e60869ba5
Source dataset
uspto-grants-2013_08
Patent number
US08519137B2

Reaction notes

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