Dimethylformamide → HCID 12790419, compound

HRID 1702877Notes

Reaction equation

HRID 1702877 reaction equation
[CH2:1]([N:17]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[C:18](=[O:21])[CH2:19][CH3:20])[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:35]=[O:36])C>>[CH:35]([C:24]1[S:23][C:22]([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:21])[CH2:19][CH3:20])=[CH:26][CH:25]=1)=[O:36]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12790414HCID 12790414, compound

Product 1

HCID 12790419HCID 12790419, compound

Procedure

75 g of N-hexadecyl-N-(2-thienyl)-propionic acid amide are dissolved in 59 cc. of anhydrous DMF and 36.7 g of phosphorus oxychloride are added thereto dropwise with ice cooling such that the temperature of the reaction mixture does not increase above 20° C. Stirring is continued for 1 hour and 20° C. and the reaction mixture finally is heated 3 hours to 80° C. Ice is added to the reaction mixture and 5 N soda lye is added until reaching a pH of 6. The resulting mixture is extracted with ether, the ethereal layer is separated, washed with water and dried over Na2SO4. The desired final product crystallizes at low temperature from the ethereal solution.

Workup

  1. temperaturedropwise with ice cooling such that the temperature of the reaction mixture does not increase above 20° C
  2. temperaturethe reaction mixture finally is heated 3 hours to 80° C
  3. additionIce is added to the reaction mixture and 5 N soda lye
  4. additionis added
  5. extractionThe resulting mixture is extracted with ether
  6. customthe ethereal layer is separated
  7. washwashed with water
  8. dry with materialdried over Na2SO4
  9. customThe desired final product crystallizes at low temperature from the ethereal solution

Sources & evidence

ORD record
ord-9035846df59d452d8a48b2b16b709fa3
Source dataset
uspto-grants-1982_09
Patent number
US04349686

Reaction notes

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