Hydrochloric Acid → HCID 86605373, compound

HRID 2387137Notes

Reaction equation

HRID 2387137 reaction equation
C([O:3][CH:4](OCC)[C:5]1[N:9]([CH3:10])[N:8]=[C:7]([CH2:11][CH3:12])[N:6]=1)C.[ClH:16]>>[OH2:3].[ClH:16].[CH2:11]([C:7]1[N:6]=[C:5]([CH:4]=[O:3])[N:9]([CH3:10])[N:8]=1)[CH3:12]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 58764230HCID 58764230, compound

Product 1

HCID 86605373HCID 86605373, compoundYield 59%

Procedure

A solution of 5-(diethoxymethyl)-3-ethyl-1-methyl-1H-1,2,4-triazole from Step 3 (35.6 g, 0.167 mol) in 3.6 M HCl (150 mL) was heated (60° C.) for 10 h, then evaporated to dryness. The residual oil was washed with THF (3×100 mL), then treated with dry acetone (200 mL) causing crystallization. The product was filtered and dried, affording 18.8 g (59%) of the title product. Satisfactory C,H,N-analysis was obtained. The compound was observed by 1H NMR to be a 60:40 mixture of non-covalent (free aldehyde) and covalent hydrates, respectively. 1H NMR (400 MHz, DMSO-d6): δ 1.22 (m, overlap, 3H), 2.67 (q, J=7.8 Hz, 0.6×2H), 2.79 (q, J=7.8 Hz, 0.4×2H), 3.96 (s, 0.4×3H), 4.04 (s, 0.6×3H), 6.21 (s, 0.4×1H), 8.35 (br s, 3H), 9.87 (s, 0.6×1H). LC-MS (APCI) calcd for C6H9N3O: 139.07, found (M+H+): 140.1; (M+18+H+) 158.1 m/z.

Workup

  1. customevaporated to dryness
  2. washThe residual oil was washed with THF (3×100 mL)
  3. additiontreated with dry acetone (200 mL)
  4. customcrystallization
  5. filtrationThe product was filtered
  6. customdried

Sources & evidence

ORD record
ord-1895b050b8c348a6b8225b1c45c75e1a
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

Loading…