4-(Hexadecylamino)benzoic acid → 4-Hexadecylaminobenzoyl chloride hydrochloride

HRID 1980158Notes

Reaction equation

HRID 1980158 reaction equation
[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=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][CH3:16].C(COC)OC.C(Cl)[Cl:34]>>[ClH:34].[CH2:1]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([Cl:34])=[O:23])=[CH:20][CH:19]=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][CH3:16]

Participants

3

Reactant 2

HCID 472634-(Hexadecylamino)benzoic acidHCID 86634710Dimethoxyethane methylene chloride

Product 1

HCID 132553224-Hexadecylaminobenzoyl chloride hydrochloride

Procedure

A cold solution of 25 g. of 4-(hexadecylamino)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 was re-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. temperatureof thionyl chloride and refluxed until all of the precipitate
  4. dissolutionwas re-dissolved
  5. customThe solvents are evaporated
  6. customto yield an orange, semi-crystalline mass

Sources & evidence

ORD record
ord-59ec298db7b54b7d8cdbec9bf336beeb
Source dataset
uspto-grants-1984_11
Patent number
US04485105

Reaction notes

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