Sodium Chloride → N-(4-cyanophenyl)-N-(4-hydroxybenzyl)-2-thiophenecarboxamide

HRID 1883695Notes

Reaction equation

HRID 1883695 reaction equation
[Si]([O:8][C:9]1[CH:31]=[CH:30][C:12]([CH2:13][N:14]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[CH:24][CH:23]=2)[C:15]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[O:16])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[Na+]>O1CCCC1>[C:28]([C:25]1[CH:24]=[CH:23][C:22]([N:14]([CH2:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:31][CH:30]=2)[C:15]([C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)=[O:16])=[CH:27][CH:26]=1)#[N:29]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 23508393N-(4-tert-butyldimethylsilyloxybenzyl)-N-(4-cyanophenyl)-2-thiophenecarboxamide

Product 1

HCID 23508471N-(4-cyanophenyl)-N-(4-hydroxybenzyl)-2-thiophenecarboxamideYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

180 mg of N-(4-tert-butyldimethylsilyloxybenzyl)-N-(4-cyanophenyl)-2-thiophenecarboxamide was dissolved in 3.5 ml of tetrahydrofuran, and 386 mg of tetrabutylammonium fluoride was added thereto under cooling with ice, followed by stirring at room temperature for 4 hours. After the reaction mixture was poured into a saturated aqueous solution of sodium chloride, the product was extracted with diethyl ether. After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by TLC (using a 19:1 mixture of chloroform and methanol as the developing solvent) to obtain 47 mg of N-(4-cyanophenyl)-N-(4-hydroxybenzyl)-2-thiophenecarboxamide.

Workup

  1. temperatureunder cooling with ice
  2. extractionthe product was extracted with diethyl ether
  3. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by TLC (
  6. additiona 19:1 mixture of chloroform and methanol as the developing solvent)

Sources & evidence

ORD record
ord-d0927adeeb474318a6bacfe637292faf
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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