4-(16-Bromohexadecylamino)benzoic acid → 4-(16-Bromohexadecylamino)benzoyl chloride hydrochloride

HRID 1106152Notes

Reaction equation

HRID 1106152 reaction equation
[Br:1][CH2:2][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:35]>>[ClH:35].[Br:1][CH2:2][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:35])=[O:24])=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 204825194-(16-Bromohexadecylamino)benzoic acidHCID 86634710Dimethoxyethane methylene chloride

Product 1

HCID 130254084-(16-Bromohexadecylamino)benzoyl chloride hydrochloride

Procedure

A cold solution of 25 g. 4-(16-bromohexadecylamino)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-b834f404c207444f9e7cd9754231dd88
Source dataset
uspto-grants-1982_01
Patent number
US04311846

Reaction notes

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