Triethyl orthoacetate → HCID 68689732, compound

HRID 1175110Notes

Reaction equation

HRID 1175110 reaction equation
[NH:1]([C:3]1[N:4]=[N:5][C:6]2[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:7]=2[N:8]=1)[NH2:2].[CH2:15](OC(OCC)(OCC)C)[CH3:16]>C(O)C>[CH3:14][O:13][C:11]1[CH:10]=[CH:9][C:7]2[N:8]3[C:15]([CH3:16])=[N:2][N:1]=[C:3]3[N:4]=[N:5][C:6]=2[CH:12]=1

Participants

4

Reactant 2

HCID 66221Triethyl orthoacetateHCID 27807653-hydrazino-7-methoxy-1,2,4-benzotriazine

Product 1

HCID 68689732HCID 68689732, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 3-hydrazino-7-methoxy-1,2,4-benzotriazine (0.5 g, 2.62 mmol) and 1,1,1-triethoxyethane (4.24 g, 26.15 mmol) was heated at 145° C. for 3 h, and the ethanol formed during the reaction was distilled off continuously. After cooling in a refrigerator for 12 h, the solid filtered off and washed with ether to give 7-methoxy-1-methyl[1,2,4]triazolo[3,4-c][1,2,4]benzotriazine (Compound Number 1, 0.5 g, 88% yield), 1H-NMR (300 MHz; CDCl3): 8.14 ppm (d, 1H, H-9); 8.14 ppm (d, 1H, H-9); 7.62 ppm (dd, 1H, H-8); 4.05 ppm (s, 3H, OMe); 3.19 ppm (s, 1H, CH3) (Compound no. 1 in table 1).

Workup

  1. distillationwas distilled off continuously
  2. temperatureAfter cooling in a refrigerator for 12 h
  3. filtrationthe solid filtered off
  4. washwashed with ether

Sources & evidence

ORD record
ord-bc590066c7e74c19bf19e39f6c9d5f5b
Source dataset
uspto-grants-2010_11
Patent number
US07838672B2

Reaction notes

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