Iodoethane → Ethyl 4-(hexadecylamino)-2-thiophenecarboxylate

HRID 850980Notes

Reaction equation

HRID 850980 reaction equation
[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([OH:25])=[O:24])[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].[H-].[Na+].[CH2:28](I)[CH3:29]>CN(C)P(N(C)C)(N(C)C)=O>[CH2:1]([NH:17][C:18]1[CH:19]=[C:20]([C:23]([O:25][CH2:28][CH3:29])=[O:24])[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

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 131349944-Hexadecylamino-2-thiophenecarboxylic acid

Product 1

HCID 20503567Ethyl 4-(hexadecylamino)-2-thiophenecarboxylate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent2×

Procedure

A solution of 7.20 g. of 4-(hexadecylamino)-2-thiophenecarboxylic acid in 25 ml. of hexamethylphosphoramide is added to a stirred mixture of 0.800 g. of sodium hydride (57% in mineral oil) and 25 ml. of hexamethylphosphoramide. The solution which forms after one hour is treated with 11.0 g. of ethyl iodide and is then stirred at 25° C. for 18 hours. Dilution with water followed by filtration affords a white solid which is crystallized from ethanol to yield ethyl 4-(hexadecylamino)-2-thiophenecarboxylate as a white solid.

Workup

  1. additionis treated with 11.0 g
  2. filtrationDilution with water followed by filtration
  3. customaffords a white solid which
  4. customis crystallized from ethanol

Sources & evidence

ORD record
ord-ae4d0f515be54256ac292198b3c7b852
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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