4-[15-(Trifluoromethyl)pentadecylamino]benzoic acid → 4-[15-(Trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride

HRID 1659917Notes

Reaction equation

HRID 1659917 reaction equation
[F:1][C:2]([F:29])([F:28])[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](O)=[O:24])=[CH:21][CH:20]=1.C(COC)OC.C(Cl)[Cl:37]>>[ClH:37].[F:1][C:2]([F:29])([F:28])[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]([Cl:37])=[O:24])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 128316104-[15-(Trifluoromethyl)pentadecylamino]benzoic acidHCID 86634710Dimethoxyethane methylene chloride

Product 1

HCID 205493174-[15-(Trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride

Procedure

A cold solution of 25 g. of 4-[15-(trifluoromethyl)-pentadecylamino]benzoic acid in 500 ml. 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. thionyl chloride and refluxed until all of the precipitate has dissolved. The solvents are evaporated to yield 4-[15-(trifluoromethyl)pentadecylamino]benzoyl chloride hydrochloride as 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. temperaturethionyl chloride and refluxed until all of the precipitate
  4. dissolutionhas dissolved
  5. customThe solvents are evaporated

Sources & evidence

ORD record
ord-1cbcf524a3f5488cbb7cd727c1236fb5
Source dataset
uspto-grants-1981_12
Patent number
US04305959

Reaction notes

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