Chloroform → N-carbobenzyloxy-4-(8-cyclohexyloctylamino)benzoyl chloride
Reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=O)=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(Cl)[Cl:26].C(=O)([O-])[O-].[Na+].[Na+].[C:35](Cl)([O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)=[O:36]>O>[C:35]([N:15]([C:16]1[CH:17]=[CH:18][C:19]([C:20]([Cl:26])=[O:22])=[CH:23][CH:24]=1)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)=[O:36]Participants
6
Conditions
- Temperature
- 40 °C
Procedure
To 15 g. 4-(8-cyclohexyloctylamino)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. 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 stirred 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-52dae928839b4bcdb68d028c1a0226d1
- Source dataset
- uspto-grants-1983_12
- Patent number
- US04423051
Reaction notes
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