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

HRID 1980175

Reaction equation

HRID 1980175 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.[C:31](=[O:34])([O-])[O-:32].[Na+].[Na+].[Cl-:37]>O>[C:31]([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:37])=[O:24])=[CH:25][CH:26]=1)([O:32][CH2:22][C:21]1[CH:25]=[CH:26][CH:18]=[CH:19][CH:20]=1)=[O:34]

Participants

6

Reactant 4

HCID 312ChlorideHCID 6212ChloroformHCID 10340Sodium CarbonateHCID 472634-(Hexadecylamino)benzoic acid

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-(n-hexadecylamino)benzoic 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. 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
  11. customevaporating each time
  12. customto yield a viscous, orange oil

Sources & evidence

ORD record
ord-3510fdf552c54acc9c2a046961c88b3f
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Linked notes

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