Chloroform → N-carbobenzyloxy-2-fluoro-4-(hexadecylamino)benzoyl chloride

HRID 1389088Notes

Reaction equation

HRID 1389088 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH:11][CH2:12][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][CH3:27])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(Cl)(Cl)[Cl:29].C(=O)([O-])[O-].[Na+].[Na+].[C:38](Cl)([O:40][CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:39]>O>[C:38]([N:11]([CH2:12][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][CH3:27])[C:9]1[CH:8]=[CH:7][C:3]([C:4]([Cl:29])=[O:6])=[C:2]([F:1])[CH:10]=1)([O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 205364112-Fluoro-4-(hexadecylamino)benzoic acid

Product 1

HCID 20536494N-carbobenzyloxy-2-fluoro-4-(hexadecylamino)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To 15 g. 2-fluoro-4-(hexadecylamino)benzoic acid in 200 ml. warm chloroform is added a solution of 15 g. of 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, ultimately to yield N-carbobenzyloxy-2-fluoro-4-(hexadecylamino)benzoyl chloride as 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

Sources & evidence

ORD record
ord-66fd73088ca34e84bb0dd3790172de08
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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