p-(15-Carbomethoxypentadecylamino)benzoic acid → 4-(15-Carbomethoxypentadecylamino)benzoyl chloride hydrochloride
Reaction equation
[C:1]([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][CH2:18][CH2:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2].C(COC)OC.C(Cl)[Cl:37]>>[ClH:37].[C:1]([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][CH2:18][CH2:19][NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([Cl:37])=[O:26])=[CH:23][CH:22]=1)([O:3][CH3:4])=[O:2]Participants
3
Procedure
A cold solution of 25 g. of 4-(15-carbomethoxypentadecylamino)benzoic acid in 500 ml. of dimethoxyethane-methylene chloride (4:1) is prepared and dry hydrochloric acid is bubbled through the solution until no more precipitate forms. The solution is treated with 25 ml. of thionyl chloride and refluxed until all of the precipitate has redissolved. The solvents are evaporated to yield an orange, semi-crystalline mass.
Workup
- customdry hydrochloric acid is bubbled through the solution until no more precipitate forms
- addition