Chloroform → HCID 21326951, compound

HRID 615053Notes

Reaction equation

HRID 615053 reaction equation
[OH:1][CH:2]([CH2:30][OH:31])[CH2:3][O:4][C:5](=[O:29])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[CH:8][CH:7]=1.[C:32](OC(=O)C)(=[O:34])[CH3:33].C(Cl)(Cl)Cl>O>[C:32]([N:12]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:9]1[CH:10]=[CH:11][C:6]([C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:30][OH:31])=[O:29])=[CH:7][CH:8]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 7918Acetic AnhydrideHCID 130193802,3-Dihydroxypropyl 4-(n-hexadecylamino)benzoate

Product 1

HCID 21326951HCID 21326951, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3.26 g. of 2,3-dihydroxypropyl-4-(n-hexadecylamino)benzoate and 0.85 ml. of acetic anhydride in 50 ml. of chloroform is heated to reflux for 1 hour and then cooled. The mixture is washed with 90 ml. of water and the solid at the interface filtered. The chloroform layer on concentration in vacuo gives a residue which on trituration with methylene chloride yields a white solid (starting material) after filtration. The filtrate on concentration in vacuo yields a pale yellow oil. The oil is stirred overnight with water, extracted with chloroform and azeotroped free of acetic acid with benzene. The pale yellow oil obtained by evaporation in high vacuum is then chromatographed to remove a trace of N,O-diacetylated material. The liquid product is characterized by elemental analyses, infrared spectrum and nuclear magnetic resonance.

Workup

  1. temperatureto reflux for 1 hour
  2. temperaturecooled
  3. washThe mixture is washed with 90 ml
  4. filtrationof water and the solid at the interface filtered
  5. concentrationThe chloroform layer on concentration in vacuo
  6. customgives a residue which on trituration with methylene chloride
  7. customyields a white solid (starting material)
  8. filtrationafter filtration
  9. concentrationThe filtrate on concentration in vacuo
  10. customyields a pale yellow oil
  11. extractionextracted with chloroform
  12. customazeotroped free of acetic acid with benzene
  13. customThe pale yellow oil obtained by evaporation in high vacuum
  14. customis then chromatographed
  15. customto remove a trace of N,O-diacetylated material

Sources & evidence

ORD record
ord-ac129d88a1d74d109e0bb6ef396e9ccd
Source dataset
uspto-grants-1979_03
Patent number
US04146546

Reaction notes

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