Hydrochloric Acid → N-(4-tert-butyl-dimethylsilyloxybenzyl)-N-(4-cyanophenyl)-3thiophenecarboxamide

HRID 1883696Notes

Reaction equation

HRID 1883696 reaction equation
[Si:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][NH:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[S:25]1[CH:29]=[CH:28][C:27]([C:30](Cl)=[O:31])=[CH:26]1.Cl>>[Si:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][N:14]([C:15]2[CH:16]=[CH:17][C:18]([C:19]#[N:20])=[CH:21][CH:22]=2)[C:30]([C:27]2[CH:28]=[CH:29][S:25][CH:26]=2)=[O:31])=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 27763773-Thenoyl chlorideHCID 235083944-[N-(4-tert-butyldimethylsilyloxybenzyl)amino]benzonitrile

Product 1

HCID 23508438N-(4-tert-butyl-dimethylsilyloxybenzyl)-N-(4-cyanophenyl)-3thiophenecarboxamideYield 71%

Procedure

The procedure of Preparation Example 8 was repeated, except that 203 mg of 4-[N-(4-tert-butyldimethylsilyloxybenzyl)amino]benzonitrile was used in place of 4-[N-(4-benzyloxybenzyl)amino]phenol and 110 mg of 3-thiophenecarbonyl chloride was used in place of methanesulfonyl chloride. The resulting mixture was stirred at room temperature for 19 hours. After the reaction mixture was poured into dilute hydrochloric acid, the product was extracted with ethyl acetate. After the extract was successively washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by TLC (using a 3:1 mixture of hexane and ethyl acetate as the developing solvent) to obtain 191 mg of N-(4-tert-butyl-dimethylsilyloxybenzyl)-N-(4-cyanophenyl)-3thiophenecarboxamide.

Workup

  1. customThe procedure of Preparation Example 8
  2. extractionthe product was extracted with ethyl acetate
  3. washAfter the extract was successively washed with a saturated aqueous solution of sodium hydrogen carbonate
  4. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by TLC (
  7. additiona 3:1 mixture of hexane and ethyl acetate as the developing solvent)

Sources & evidence

ORD record
ord-750a509b7d2443679c54dfdb3299df78
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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