Methanol → HCID 178481921, compound

HRID 2382147Notes

Reaction equation

HRID 2382147 reaction equation
[N:1]1[N:2]=[CH:3][N:4]2[C:17]=1[C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1.CO.[F:20][B-:21]([F:24])([F:23])[F:22].[CH3:25][O+](C)C>ClCCl>[F:20][B-:21]([F:24])([F:23])[F:22].[CH3:25][N+:1]1[N:2]=[CH:3][N:4]2[C:17]=1[C:16]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]2=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1403098HCID 1403098, compoundHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

Product 1

HCID 178481921HCID 178481921, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
2 °C

Procedure

A solution of 1,2,4-triazolo[4,3-f]phenanthridine (A. G. Mikhailovskii, V. S. Shklyaev, Chem. Heterocycl. Comp. 1992, 445) (5.9 g, 27 mmol) in dichloromethane (200 ml) and methanol (20 ml) is admixed under argon at 2° C. with trimethyloxonium tetrafluoroborate (4.3 g, 29 mmol) and stirred at 2° C. for 1 h and at room temperature for 16 h. The resulting precipitate is filtered off and washed with dichloromethane, methanol and petroleum ether. Yield: 5.9 g (69%).

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with dichloromethane, methanol and petroleum ether

Sources & evidence

ORD record
ord-ca31ac9a3bf64cf686b4e80df3c7f0d2
Source dataset
uspto-grants-2012_09
Patent number
US08258297B2

Reaction notes

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