4-(8-Cyclohexyloctylamino)benzoic acid → p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride

HRID 905269Notes

Reaction equation

HRID 905269 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](O)=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(COC)OC.C(Cl)[Cl:32]>>[ClH:32].[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]([Cl:32])=[O:21])=[CH:18][CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 204757724-(8-Cyclohexyloctylamino)benzoic acidHCID 86634710Dimethoxyethane methylene chloride

Product 1

HCID 20475769p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride

Procedure

A cold solution of 25 g. of 4-(8-cyclohexyloctylamino)-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 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
  6. customto yield an orange, semi-crystalline mass

Sources & evidence

ORD record
ord-8fe3de497288448c8e503191a9e80e5a
Source dataset
uspto-grants-1983_12
Patent number
US04423051

Reaction notes

Loading…