Methane → HCID 12799945, compound

HRID 2412624Notes

Reaction equation

HRID 2412624 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[C:8](=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[NH:22]1[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:31]([O:33][CH3:34])=[O:32])[CH:29]=2)[CH:24]=[CH:23]1.C>CO>[C:8]([C:24]1[C:25]2[C:30](=[CH:29][C:28]([C:31]([O:33][CH3:34])=[O:32])=[CH:27][CH:26]=2)[NH:22][CH:23]=1)(=[O:20])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 297MethaneHCID 18159N,N-DimethyldodecanamideHCID 24813Phosphorus oxychlorideHCID 639844Methyl indole-6-carboxylate

Product 1

HCID 12799945HCID 12799945, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

Phosphorus oxychloride (27.5 ml) was added dropwise during 20 minutes to stirred N,N-dimethyldodecanamide (84.9 g) at room temperature. The temperature of the mixture rose during the addition to 50° C. The mixture was stirred and heated at 90° C. for 15 minutes and then methyl indole-6-carboxylate (33.4 g) was added portionwise to the stirred mixture during 10 minutes, the temperature of the mixture being maintained at 90° C. during the addition. The mixture was then stirred for 2 hours at 90° C. and was then poured onto ice. The aqueous mixture was extracted with chloroform (3×300 ml) and the extract was dried over magnesium sulphate and was evaporated to give a red brown oil. The oil was dissolved in boiling methanol (100 ml), the solution was treated with charcoal and the solution was filtered and cooled (0° C.) to give methyl 3-(n-dodecanoyl)indole-6-carboxylate (26.7 g), in the form of a buff solid, m.p. 167°-169° C.

Workup

  1. additionThe temperature of the mixture rose during the addition to 50° C
  2. temperaturethe temperature of the mixture being maintained at 90° C. during the addition
  3. stirringThe mixture was then stirred for 2 hours at 90° C.
  4. additionwas then poured onto ice
  5. extractionThe aqueous mixture was extracted with chloroform (3×300 ml)
  6. dry with materialthe extract was dried over magnesium sulphate
  7. customwas evaporated
  8. customto give a red brown oil
  9. dissolutionThe oil was dissolved
  10. filtrationthe solution was filtered
  11. temperaturecooled (0° C.)

Sources & evidence

ORD record
ord-ed7d77e8dd154a4ebd713f88ac5e5521
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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