Chloroform → HCID 13386683, compound

HRID 745460Notes

Reaction equation

HRID 745460 reaction equation
[CH2:1]([O:17][CH2:18][CH:19]([OH:23])[CH2:20][NH:21][CH3:22])[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(Cl)(Cl)Cl.[C:28](Cl)(=[O:30])[CH3:29]>C(N(CC)CC)C>[C:28]([N:21]([CH3:22])[CH2:20][CH:19]([OH:23])[CH2:18][O: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])(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6367Acetyl chlorideHCID 12591561HCID 12591561, compound

Product 1

HCID 13386683HCID 13386683, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

5 g of 1-hexadecyloxy-3-methylamino-propan-2-ol are dissolved in 30 cc. of anhydrous chloroform. At first 3 g of triethylamine and separately thereafter 2.4 g of acetylchloride are added dropwise with cooling and the mixture is stirred for 8 hours. The chloroform solution is washed with 2% hydrochloric acid and water, is evaporated and the residue is dissolved in 100 cc. of methanol. A solution of 0.6 g of sodium hydroxide in a little methanol is added to the methanol solution and the mixture is stirred at room temperature for one hour. The solvent is evaporated in a vacuo and the residue is triturated in chloroform. The chloroform solution is washed with 2% hydrochloric acid and water, is dried over sodium sulfate and is evaporated.

Workup

  1. temperaturewith cooling
  2. washThe chloroform solution is washed with 2% hydrochloric acid and water
  3. customis evaporated
  4. dissolutionthe residue is dissolved in 100 cc
  5. additionA solution of 0.6 g of sodium hydroxide in a little methanol is added to the methanol solution
  6. stirringthe mixture is stirred at room temperature for one hour
  7. customThe solvent is evaporated in a vacuo
  8. customthe residue is triturated in chloroform
  9. washThe chloroform solution is washed with 2% hydrochloric acid and water
  10. dry with materialis dried over sodium sulfate
  11. customis evaporated

Sources & evidence

ORD record
ord-6432f0d709d14f2ca86d945be1ad4e70
Source dataset
uspto-grants-1986_07
Patent number
US04599205

Reaction notes

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