4-Hexadecylamino-2-thiophenecarboxylic acid → 4-Hexadecylamino-2-thiophenecarbonyl chloride hydrochloride

HRID 850978Notes

Reaction equation

HRID 850978 reaction equation
[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([OH:25])=O)[S:21][CH:22]=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].COCCOC.C(Cl)[Cl:33]>>[ClH:33].[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([Cl:33])=[O:25])[S:21][CH:22]=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 131349944-Hexadecylamino-2-thiophenecarboxylic acidHCID 86634710Dimethoxyethane methylene chloride

Product 1

HCID 205036504-Hexadecylamino-2-thiophenecarbonyl chloride hydrochloride

Procedure

A cold solution of 25 g. of 4-hexadecylamino-2-thiophenecarboxylic acid in 500 ml. of 1,2-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 the product 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
  6. customto yield the product as an orange semi-crystalline mass

Sources & evidence

ORD record
ord-b95909518da2469a90cecff9767cd7d7
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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