Hydrochloric Acid → HCID 23508514, compound

HRID 1883677Notes

Reaction equation

HRID 1883677 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([NH:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH:5]=1.C[Si](C)(C)[O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1.Cl.C(=O)([O-])O.[Na+]>C(Cl)Cl.C(N(CC)CC)C>[C:11]([C:10]1[CH:9]=[CH:8][C:7]([N:6]([N:4]2[CH:3]=[N:2][N:1]=[CH:5]2)[C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([OH:17])=[CH:19][CH:20]=2)=[CH:14][CH:13]=1)#[N:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 10307909Benzonitrile, 4-(4H-1,2,4-triazol-4-ylamino)-HCID 12726254HCID 12726254, compound

Product 1

HCID 23508514HCID 23508514, compoundYield 36.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture composed of 10.43 g of 4-[N-(1,2,4-triazol-4-yl)amino]benzonitrile, 7.9 ml of triethylamine, and 56 ml of methylene chloride was stirred under cooling with ice, and a mixture composed of 23.7 g of 4-(trimethylsilyloxy)benzoyl chloride and 28 ml of methylene chloride was added dropwise thereto, followed by stirring at room temperature for 1 hour. Dilute hydrochloric acid was added to the reaction mixture, followed by stirring at room temperature overnight. After the reaction mixture was neutralized with a saturated aqueous solution of sodium hydrogen carbonate, the product was extracted with tetrahydrofuran-diethyl ether (1:1). After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (using a 4:1 mixture of chloroform and acetone as the eluent) to obtain 6.2 g of N-(4-cyanophenyl)-4-hydroxy-N-(1,2,4-triazol-4-yl)benzamide.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added dropwise
  3. stirringby stirring at room temperature for 1 hour
  4. stirringby stirring at room temperature overnight
  5. extractionthe product was extracted with tetrahydrofuran-diethyl ether (1:1)
  6. washAfter the extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting crude product was purified by silica gel column chromatography (
  10. additiona 4:1 mixture of chloroform and acetone as the eluent)

Sources & evidence

ORD record
ord-e3ee5ab91ebc4f8daf7d78a7cd81c58e
Source dataset
uspto-grants-2004_07
Patent number
US06762205B1

Reaction notes

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