Methane → HCID 10932009, compound

HRID 1650694Notes

Reaction equation

HRID 1650694 reaction equation
[CH3:1][N:2]1[CH:6]=[N:5][C:4]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:3]1.[BH4-].[Na+].[CH4:15]>CO.[Cl-].[Na+].CCOCC>[CH3:1][N:2]1[CH:6]=[N:5][C:4]([C:7]2[CH2:8][N:9]([CH3:15])[CH2:10][CH2:11][CH:12]=2)=[N:3]1

Participants

7

Reactant 3

HCID 297MethaneHCID 4311764Sodium borohydrideHCID 19612506HCID 19612506, compound

Product 1

HCID 10932009HCID 10932009, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 5234Sodium ChlorideSolvent

Conditions

Temperature
-10 °C

Procedure

A suspension of 6.3 g (0.020 mol) of the methiodide of 57 (prepared from 57 by the procedure described in Example 1) in 75 ml of methanol was cooled to -10° C., and 1.0 g (0.026 mol) of sodium borohydride was added. When the gas evolution had ceased, the mixture was stirred for 3 h at room temperature. Evaporation in vacuo gave a red oil which was dissolved in 100 ml of a saturated sodium chloride solution. Extraction with 4×100 ml of dichloromethane, drying of the organic phase over magnesium sulfate, and evaporation in vacuo gave a red oil. The oil was dissolved in 50 ml of ether and stirred with charcoal. Filtration and evaporation gave the base of 59 as a colorless oil, 58. Yield: 1.6 g (0.009 mol, 45%). A 0.5 g portion of 58 was converted to the title compound. M.P. 181°-183° C. Anal. (C11H16N4O2) C, H, N.

Workup

  1. customprepared from 57 by the procedure
  2. customEvaporation in vacuo
  3. customgave a red oil which
  4. extractionExtraction with 4×100 ml of dichloromethane
  5. dry with materialdrying of the organic phase over magnesium sulfate, and evaporation in vacuo
  6. customgave a red oil
  7. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-21ae9ce3c0494ac1a10578cd4e35dcf1
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

Loading…