Dimethylformamide → HCID 12790418, compound

HRID 1702876Notes

Reaction equation

HRID 1702876 reaction equation
[CH2:1]([N:17]([C:21]1[S:22][CH:23]=[CH:24][CH:25]=1)[C:18](=[O:20])[CH3:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].P(Cl)(Cl)(Cl)=O.CN([CH:34]=[O:35])C>>[CH:34]([C:23]1[S:22][C:21]([N:17]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[C:18](=[O:20])[CH3:19])=[CH:25][CH:24]=1)=[O:35]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12790413HCID 12790413, compound

Product 1

HCID 12790418HCID 12790418, compound

Procedure

27 g of N-Hexadecyl-N-(2-thienyl)-acetamide are dissolved in 22 cc. of anhydrous DMF and 14 g of phosphorus oxychloride are added dropwise thereto under cooling with ice, thereby avoiding increase of the temperature of the reaction mixture above 20° C. Stirring is continued for 1 hour at 20° C. and the reaction mixture finally is stirred for 3 hours at 80° C. Ice is added to the reaction mixture and 5 N soda lye is added thereto until reaching a pH of 6. The resulting mixture is extracted with ether, the ethereal phase is separated, washed with water and dried over Na2SO4. The ether is separated and the residue is purified chromatographically on a column of silicic acid gel using hexane/ethyl acetate as eluant.

Workup

  1. temperatureunder cooling with ice
  2. temperatureavoiding increase of the temperature of the reaction mixture above 20° C
  3. stirringthe reaction mixture finally is stirred for 3 hours at 80° C
  4. additionIce is added to the reaction mixture and 5 N soda lye
  5. additionis added
  6. extractionThe resulting mixture is extracted with ether
  7. customthe ethereal phase is separated
  8. washwashed with water
  9. dry with materialdried over Na2SO4
  10. customThe ether is separated
  11. customthe residue is purified chromatographically on a column of silicic acid gel

Sources & evidence

ORD record
ord-e27524f571b54c259939c847f6688e48
Source dataset
uspto-grants-1982_09
Patent number
US04349686

Reaction notes

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