p-(15-Carbomethoxypentadecylamino)benzoic acid → 4-(15-Carbomethoxypentadecylamino)benzoyl chloride hydrochloride

HRID 1278396Notes

Reaction equation

HRID 1278396 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

Reactant 2

HCID 12898273p-(15-Carbomethoxypentadecylamino)benzoic acidHCID 86634710Dimethoxyethane methylene chloride

Product 1

HCID 211632694-(15-Carbomethoxypentadecylamino)benzoyl chloride hydrochloride

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

  1. customdry hydrochloric acid is bubbled through the solution until no more precipitate forms
  2. additionThe solution is treated with 25 ml
  3. temperatureof thionyl chloride and refluxed until all of the precipitate
  4. dissolutionhas redissolved
  5. customThe solvents are evaporated
  6. customto yield an orange, semi-crystalline mass

Sources & evidence

ORD record
ord-72cfbebc9e944b55a3521cfe00f2f0da
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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