Ethyl orthoformate → HCID 11529091, compound

HRID 1175111Notes

Reaction equation

HRID 1175111 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]=[C:7]([NH:11][NH2:12])[N:8]=[N+:9]([O-:10])[C:4]=2[CH:3]=1.[CH2:15](OC(OCC)OCC)C>C(O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]3[CH:15]=[N:12][N:11]=[C:7]3[N:8]=[N+:9]([O-:10])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 13582957872459-81-5

Product 1

HCID 11529091HCID 11529091, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 7-bromo-3-hydrazino-1,2,4-benzotriazine 1-oxide (1 g, 3.91 mmol) and 1,1,1-triethoxymethane (6.24 g, 42.08 mmol) was heated to 145° C. for 3 h, and the ethanol formed during the reaction was continuously distilled off. After cooling in a refrigerator for 12 h, the solid filtered off and washed with ether to give 7-bromo[1,2,4]triazolo[3,4-c][1,2,4]benzotriazine-5-oxide, (Compound Number 5, 0.68 g, 63% yield), 1H-NMR (300 MHz; DMSO): 9.95 ppm (s,1H, H-1); 8.60 ppm (d,1H, H-6); 8.47 ppm (d, 1H, H-9) and 8.38 ppm (dd,1H, H-8).

Workup

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

Sources & evidence

ORD record
ord-29e0c35110254758ab11276aa1f756d7
Source dataset
uspto-grants-2010_11
Patent number
US07838672B2

Reaction notes

Loading…