Chloride → N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

HRID 262919

Reaction equation

HRID 262919 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=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.O.[C:32](=[O:35])([O-])[O-:33].[Na+].[Na+].[Cl-:38]>O>[C:32]([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]([C:22]([Cl:38])=[O:24])=[CH:25][CH:26]=1)([O:33][CH2:22][C:21]1[CH:25]=[CH:26][CH:18]=[CH:19][CH:20]=1)=[O:35]

Participants

6

Reactant 4

HCID 312ChlorideHCID 10340Sodium CarbonateHCID 472634-(Hexadecylamino)benzoic acidHCID 22418719Chloroform water

Product 1

HCID 20437379N-carbobenzyloxy-4-(hexadecylamino)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 15 g. of 4-(hexadecylamino)benzoic acid in 200 ml. water chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously stirred solution is added 10 g. carbobenzoyl chloride. After 2 hours stirring at 40° C., the layers are separated, washed three times with 1N hydrochloric acid, dried, and evaporated to an oil. The oil is dissolved in 300 ml. toluene, treated with 15 ml. of 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 1N hydrochloric acid
  4. customdried
  5. customevaporated to an oil
  6. dissolutionThe oil is dissolved in 300 ml
  7. additiontoluene, treated with 15 ml
  8. temperatureof thionyl chloride, and the solution is refluxed for 5 hours
  9. customThe solvents are evaporated
  10. dissolutionthe residue is dissolved three times in toluene evaporating each time
  11. customto yield a viscous, orange oil

Sources & evidence

ORD record
ord-215a47255d3743f5982cad93885e562e
Source dataset
uspto-grants-1979_05
Patent number
US04154756

Linked notes

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