Hydrochloric Acid → HCID 178527117, compound

HRID 2267047Notes

Reaction equation

HRID 2267047 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])(C)(C)C.[N:18]1C=CC=CC=1.[S:24](Cl)(Cl)=[O:25].Cl.[Cl-].[Na+].[OH2:31]>C(O)(C)C.O1CCCC1.ClCCl>[O:31]=[S:24]1[NH:12][C:11]([C:10]2[CH:9]=[C:8]([CH2:7][OH:6])[CH:15]=[CH:14][CH:13]=2)=[N:18][O:25]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 57417360Sodium chloride; waterHCID 178455426HCID 178455426, compound

Product 1

HCID 178527117HCID 178527117, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add hydroxylainine (50% aqueous solution, 5.34 g, 80.8 mmol) dropwise to a refluxing solution of 3-(tert-butyl-dimethyl-silanyloxymethyl)-benzonitrile (5.00 g, 20.2 mmol) in isopropanol (0.1 M). After 2 hours, concentrate the reaction under reduced pressure and azeotrope with toluene. Add dichloromethane (0.1 M) and pyridine (1.92 g, 24.3 mmol) and cool reaction to −78° C. Add thionyl chloride (2.64 g, 22.2 mmol) via syringe. After 4 hours, warm the reaction to room temperature. Concentrate the reaction under reduced pressure. Add tetrahydrofuran (0.1M) and 10% hydrochloric acid (0.1M) and stir. After 18 hours, add brine and extract with 25% isopropyl alcohol:75% dichloromethane. Combine organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title product as a yellow solid (3.90 g, 91%): 1H NMR (DMSO-d6) δ 4.63 (s, 2H), 5.42 (bs, 1H), 7.59 (m, 2H), 7.75 (dt, 1H), 7.88 (s, 1H), 12.23 (bs, 1H).

Workup

  1. concentrationconcentrate
  2. customthe reaction under reduced pressure and azeotrope with toluene
  3. customreaction to −78° C
  4. waitAfter 4 hours
  5. temperaturewarm
  6. customthe reaction to room temperature
  7. concentrationConcentrate
  8. customthe reaction under reduced pressure
  9. waitAfter 18 hours
  10. extractionextract with 25% isopropyl alcohol
  11. dry with materialCombine organic layers, dry with sodium sulfate
  12. filtrationfilter
  13. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-1b1b4e459e4747289d4acb474cdf2a04
Source dataset
uspto-grants-2010_12
Patent number
US07858646B2

Reaction notes

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