Hydrochloric Acid → 4-Hexadecylamino-2-thiophenecarboxylic acid

HRID 850962Notes

Reaction equation

HRID 850962 reaction equation
[C:1]([C:4]1[S:5][CH:6]=[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:8]=1)(=[O:3])N.Cl.C[O:28]CCO>>[CH2:10]([NH:9][C:7]1[CH:8]=[C:4]([C:1]([OH:28])=[O:3])[S:5][CH:6]=1)[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 80192-MethoxyethanolHCID 131349932-Carbamyl-4-hexadecylaminothiophene

Product 1

HCID 131349944-Hexadecylamino-2-thiophenecarboxylic acid

Procedure

A mixture of 4.4 g. of 2-carbamyl-4-hexadecylaminothiophene, 50 ml. of methyl cellosolve, and 50 ml. of 6 N hydrochloric acid is refluxed for 40 hours and then allowed to cool. The solid is filtered and recrystallized from methanol. The solid is then dissolved in hot sodium bicarbonate solution, filtered, and the filtrate is acidified with concentrated hydrochloric acid. The resulting precipitate is collected and recrystallized from isopropanol to yield the product.

Workup

  1. additionA mixture of 4.4 g
  2. temperatureto cool
  3. filtrationThe solid is filtered
  4. customrecrystallized from methanol
  5. dissolutionThe solid is then dissolved in hot sodium bicarbonate solution
  6. filtrationfiltered
  7. customThe resulting precipitate is collected
  8. customrecrystallized from isopropanol
  9. customto yield the product

Sources & evidence

ORD record
ord-77c3e18d0c7043d184750298c932b43d
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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