Chloroform → N-Carbobenzyloxy-4-(hexadecylamino)cinnamoyl chloride

HRID 1702698Notes

Reaction equation

HRID 1702698 reaction equation
[CH2:1]([NH:17][C:18]1[CH:28]=[CH:27][C:21]([CH:22]=[CH:23][C:24]([OH:26])=O)=[CH:20][CH:19]=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(Cl)(Cl)[Cl:30].C(=O)([O-])[O-].[Na+].[Na+].[C:39](Cl)([O:41][CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)=[O:40]>O>[C:39]([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]1[CH:19]=[CH:20][C:21]([CH:22]=[CH:23][C:24]([Cl:30])=[O:26])=[CH:27][CH:28]=1)([O:41][CH2:42][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1)=[O:40]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 539289584-Hexadecylaminocinnamic acid

Product 1

HCID 54240268N-Carbobenzyloxy-4-(hexadecylamino)cinnamoyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 15 g. 4-(hexadecylamino)cinnamic acid in 200 ml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. carbobenzyloxy chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1 N hydrochloric acid, dried, and evaporated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. thionyl chloride and the solution is refluxed for 5 hours. The solvents are evaporated and the residue is dissolved three times in toluene, evaporating each time to yield a viscous, orange oil.

Workup

  1. additionTo the vigorously stirred solution is added 10 g
  2. customthe layers are separated
  3. washwashed three times with 1 N hydrochloric acid
  4. customdried
  5. customevaporated to an oil
  6. dissolutionThe oil is dissolved in 300 ml
  7. additiontoluene, treated with 15 ml
  8. temperaturethionyl chloride and the solution is refluxed for 5 hours
  9. customThe solvents are evaporated
  10. dissolutionthe residue is dissolved three times in toluene
  11. customevaporating each time
  12. customto yield a viscous, orange oil

Sources & evidence

ORD record
ord-3667c88f6e6f4d83b96d28f52d047dc9
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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