Triethyl orthoacetate → HCID 19349977, compound

HRID 42051Notes

Reaction equation

HRID 42051 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([NH:7][NH2:8])=[O:6].[CH2:12](OC(OCC)(OCC)C)[CH3:13]>C(O)(=O)C>[I:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:12]([CH3:13])=[N:8][N:7]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 6157743-Iodobenzohydrazide

Product 1

HCID 19349977HCID 19349977, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
150 °C

Procedure

In a schlenck tube, a mixture of 3-iodobenzohydrazide (510 mg, 1.95 mmol) and 1,1,1-triethoxyethane (1.14 ml, 6.23 mmol) in acetic acid (15 ml) was heated at 150° C. for 3 h. The solvent was evaporated and the crude redissolved in ethyl acetate and washed with 4% solution of NaHCO3, water and brine. The organic layer was dried, filtered and concentrated under vacuum to give the title compound as a white solid (92% yield).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude redissolved in ethyl acetate
  3. washwashed with 4% solution of NaHCO3, water and brine
  4. customThe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b834c3bf6f8e474790aa81fa7c23d952
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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