Dimethylformamide → HCID 12790420, compound

HRID 1702878Notes

Reaction equation

HRID 1702878 reaction equation
[CH2:1]([N:17]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[C:18](=[O:22])[CH2:19][CH2:20][CH3:21])[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:36]=[O:37])C>>[CH:36]([C:25]1[S:24][C:23]([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:22])[CH2:19][CH2:20][CH3:21])=[CH:27][CH:26]=1)=[O:37]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 12790415HCID 12790415, compound

Product 1

HCID 12790420HCID 12790420, compound

Procedure

78 g of N-hexadecyl-N-(2-thienyl)-butyric acid amide are dissolved in 59 cc. of anhydrous DMF and 36.7 g of phosphorus oxychloride are added thereto with ice cooling such that the temperature of the reaction mixture does not rise above 20° C. Stirring is continued for 1 hour at 20° C. and the mixture is finally heated for 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 mixture is extracted with ether, the ethereal layer is separated, washed with water and dried over Na2SO4. The desired final product crystallizes from the ethereal solution upon cooling to low temperature.

Workup

  1. customdoes not rise above 20° C
  2. temperaturethe mixture is finally heated for 3 hours to 80° C
  3. additionIce is added to the reaction mixture and 5 N soda lye
  4. additionis added
  5. extractionThe 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 from the ethereal solution
  10. temperatureupon cooling to low temperature

Sources & evidence

ORD record
ord-4d25a658bd714c3b87f7afe07a3053bd
Source dataset
uspto-grants-1982_09
Patent number
US04349686

Reaction notes

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