Methane → HCID 54395952, compound

HRID 477716Notes

Reaction equation

HRID 477716 reaction equation
CN(C)[CH:3]=[O:4].P(Cl)(Cl)(Cl)=O.[I-].[CH2:12]([C:16]1([CH2:27][CH:28]([CH3:30])[CH3:29])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N+:18]([CH3:25])=[C:17]1[CH3:26])[CH:13]([CH3:15])[CH3:14].C>O>[CH2:12]([C:16]1([CH2:27][CH:28]([CH3:30])[CH3:29])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]([CH3:25])[C:17]1=[CH:26][CH:3]=[O:4])[CH:13]([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 297MethaneHCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 19872252HCID 19872252, compound

Product 1

HCID 54395952HCID 54395952, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 10 mL of dry dimethylformamide in a flask cooled with an ice bath was added dropwise with stirring phosphoryl chloride (1.76 g, 0.0115 mole). After a few minutes 3,3-diisobutyl-1,2-dimethyl-(3H)-indolium iodide (3.85 g, 0.01 mole) was added portionwise over 5 min. The resulting solution was allowed to stir at room temperature for at least 3 hours. This solution was then slowly poured into 250 mL of water stirring in a beaker. After a few minutes 3,3-diisobutyl-2-dimethylaminovinyl-1-methyl-(3H)-indolium iodide separated as its monohydrate via elemental analysis and NMR of a small sample which was removed. This aqueous suspension was then heated to boiling with stirring to dissolve this intermediate product giving a yellow solution with a little purple scum floating on the top. A little Norit was added and after a minute or so the solution was filtered. The yellow filtrate was made strongly basic with 20% sodium hydroxide solution and stirred with warming at 50°-60° C. for a few minutes. The formylmethylene product separated and slowly became crystalline. After cooling to room temperature, the product was filtered, washed well with water, and dried to give 2.3 g (80.6%). The IR and NMR were good. (MW 285.43)

Workup

  1. customAfter a few minutes 3,3-diisobutyl-2-dimethylaminovinyl-1-methyl-(3H)-indolium iodide separated as its monohydrate via elemental analysis and NMR of a small sample which
  2. customwas removed
  3. temperatureThis aqueous suspension was then heated
  4. stirringwith stirring
  5. dissolutionto dissolve this intermediate product
  6. customgiving a yellow solution with a little purple scum
  7. filtrationafter a minute or so the solution was filtered
  8. stirringstirred
  9. temperaturewith warming at 50°-60° C. for a few minutes
  10. customThe formylmethylene product separated
  11. temperatureAfter cooling to room temperature
  12. filtrationthe product was filtered
  13. washwashed well with water
  14. customdried
  15. customto give 2.3 g (80.6%)

Sources & evidence

ORD record
ord-989a904eae2248338bb9ee488d8fc682
Source dataset
uspto-grants-1989_12
Patent number
US04889410

Reaction notes

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