Chloroform → N-Carbobenzyloxy-4-(16-bromohexadecylamino)benzoyl chloride
Reaction equation
[Br: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][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=O)=[CH:21][CH:20]=1.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:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[C:19]1[CH:20]=[CH:21][C:22]([C:23]([Cl:29])=[O:25])=[CH:26][CH:27]=1)([O:40][CH2:41][C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)=[O:39]Participants
6
Conditions
- Temperature
- 40 °C
Procedure
To 15 g. 4-(16-bromohexadecylamino)benzoic acid in 200 ml. warm chloroform is added 15 g. sodium carbonate in 150 ml. water. To the vigorously 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
- additionTo the vigorously solution is added 10 g
- customthe layers are separated
- washwashed three times with 1 N hydrochloric acid
- customdried
- customevaporated to an oil
- dissolutionThe oil is dissolved in 300 ml
- additiontoluene, treated with 15 ml
- temperaturethionyl chloride and the solution is refluxed for 5 hours
- customThe solvents are evaporated
- dissolutionthe residue is dissolved three times in toluene
- customevaporating each time
- customto yield a viscous, orange oil
Sources & evidence
- ORD record
- ord-c2ad4e770f0e4a43945f5f4da6bae0c9
- Source dataset
- uspto-grants-1983_10
- Patent number
- US04411903
Reaction notes
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