Triethylamine → HCID 178500187, compound

HRID 870573Notes

Reaction equation

HRID 870573 reaction equation
C(N(CC)CC)C.[NH:8]=[C:9](OC)[CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15].[CH:20]([NH:22][NH2:23])=O>CO>[N:22]1[N:23]=[C:9]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])[NH:8][CH:20]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12229HydrazinecarboxaldehydeHCID 23189824Methyl 6-imino-6-methoxyhexanoate

Product 1

HCID 178500187HCID 178500187, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Add methanol (1 mL) and triethylamine (0.36 mL; 1.0 equiv; 2.58 mmoles) to a vial containing methyl 6-imino-6-methoxy-hexanoate (0.542 g; 1.00 equiv; 2.58 mmoles), followed by a solution of formylhydrazine (0.155 g 1.0 equiv; 2.58 mmoles) in methanol (3 mL). Stir at room temperature for 18 hours, then heat to 70° C. for 3 hours. Concentrate the mixture, then dilute with ethyl acetate (30 mL) and filter. Concentrate the filtrate to afford methyl 5-(4H-1,2,4-triazol-3-yl)pentanoate (0.498 g; 105%) as a colorless oil: MS (m/z): 184 (M+1).

Workup

  1. temperatureheat to 70° C. for 3 hours
  2. concentrationConcentrate the mixture
  3. additiondilute with ethyl acetate (30 mL)
  4. filtrationfilter
  5. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-b26e52f6748241e49c33a95994dd05b0
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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