Methyl iodide → 9-Methoxy-3,4-diazatricyclo[4,2,1,02,5]-nona-3,7-diene

HRID 1981099Notes

Reaction equation

HRID 1981099 reaction equation
[H-].[Na+].[OH:3][CH:4]1[CH:10]2[CH:11]=[CH:12][CH:5]1[CH:6]1[CH:9]2[N:8]=[N:7]1.[CH3:13]I>C(#N)C>[CH3:13][O:3][CH:4]1[CH:10]2[CH:11]=[CH:12][CH:5]1[CH:6]1[CH:9]2[N:8]=[N:7]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70539013HCID 70539013, compound

Product 1

HCID 860899439-Methoxy-3,4-diazatricyclo[4,2,1,02,5]-nona-3,7-diene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1 part of NaH was added, a little at a time, to 5 parts of 9-hydroxy-3,4-diazatricyclo[4,2,1,02,5 ]nona-3,7-diene and 100 parts of acetonitrile at 20° C., while stirring. Thereafter, 20 parts of methyl iodide were added and stirring was continued for 12 hours at 20° C. The reaction mixture was evaporated down in a rotary evaporator at from 20° to 50° C. and under 20 mbar, and the residue was extracted with 200 parts of petroleum ether. The petroleum ether phase was evaporated down to give 5 parts (90 mole %) of 9-methoxy-3,4-diazatricyclo[4,2,1,02,5 ]-nona-3,7-diene as an oil. 1H-NMR (δ in ppm): 6.2 (bs, 2H), 4.1 (bs, 2H), 3.1-3.3 (m, 6H).

Workup

  1. customThe reaction mixture was evaporated down in a rotary evaporator at from 20° to 50° C. and under 20 mbar
  2. extractionthe residue was extracted with 200 parts of petroleum ether
  3. customThe petroleum ether phase was evaporated down

Sources & evidence

ORD record
ord-82b75eacf31640a4a4ec6dd47aa28ec6
Source dataset
uspto-grants-1985_04
Patent number
US04512795

Reaction notes

Loading…