2-Thiophenecarboxylic acid → N-(3,5-Diethyl-4-hydroxyphenyl)thiophene-2-carboxamide

HRID 728343Notes

Reaction equation

HRID 728343 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([OH:8])=O.C(OP(Cl)(=O)OCC)C.[NH2:18][C:19]1[CH:24]=[C:23]([CH2:25][CH3:26])[C:22]([OH:27])=[C:21]([CH2:28][CH3:29])[CH:20]=1.C(=O)([O-])O.[Na+]>C(#N)C.C(N(CC)CC)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([NH:18][C:19]1[CH:20]=[C:21]([CH2:28][CH3:29])[C:22]([OH:27])=[C:23]([CH2:25][CH3:26])[CH:24]=1)=[O:8]

Participants

7

Reactant 4

HCID 107002-Thiophenecarboxylic acidHCID 13139Diethyl chlorophosphateHCID 516892Sodium BicarbonateHCID 14551563HCID 14551563, compound

Product 1

HCID 14939587N-(3,5-Diethyl-4-hydroxyphenyl)thiophene-2-carboxamideYield 54.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

Under ice-cooling, 128 mg of 2-thienylcarboxylic acid is dissolved in 3 ml of acetonitrile, and to the resultant solution are added 303 mg of triethylamine, then 207 mg of diethylphosphorochloridate. After the mixture is stirred for 30 minutes, 201 mg of 4-amino-2,6-diethylphenol is added and the reaction mixture is stirred at room temperature. After completion of the reaction, ice chips are added, and then an aqueous 5 % sodium hydrogen carbonate is added. The crystals precipitated are collected by filtration, washed with isopropyl ether and the residue is recrystallized from ethyl acetate to give 150 mg of 4-(2-thienylcarbonyl)amino-2,6-diethylphenol as white crystals.

Workup

  1. temperatureUnder ice-cooling
  2. stirringthe reaction mixture is stirred at room temperature
  3. customAfter completion of the reaction, ice chips
  4. additionare added
  5. customThe crystals precipitated
  6. filtrationare collected by filtration
  7. washwashed with isopropyl ether
  8. customthe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3f1682c421ce49e3bf53fc9b5ed91400
Source dataset
uspto-grants-1991_09
Patent number
US05047555

Reaction notes

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