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

HRID 904251Notes

Reaction equation

HRID 904251 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-24d483e144804dbeb17bc3d9d16052d6
Source dataset
uspto-grants-1980_10
Patent number
US04230628

Reaction notes

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