Sodium Hydroxide → HCID 14372824, compound

HRID 359697Notes

Reaction equation

HRID 359697 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[C:8](#[N:16])[C:9]1[C:10](=[CH:12][CH:13]=[CH:14][CH:15]=1)[NH2:11].[OH-].[Na+]>[Cl-].[Cl-].[Zn+2].CC(=O)CC>[NH2:16][C:8]1[C:9]2[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=2[N:11]=[C:4]2[CH2:3][CH2:2][S:1][CH2:6][C:5]=12

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 66173Tetrahydrothiopyran-4-oneHCID 729132-Aminobenzonitrile

Product 1

HCID 14372824HCID 14372824, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Tetrahydrothiopyran-4one (10.0 g) was mixed with anthranilonitrile (5.08 g) and the mixture warmed at 60° until a homogeneous solution was obtained. Freshly fused ZnCl2 (8.2 g) was then added portionwise and the temperature of the reaction mixture raised to 120°. After 2 hours it was cooled and distributed between 10% NaOH and 2-butanone. The organic phase was separated, dried, and concentrated and the crude product triturated with Et2O and then passed over a silica gel column (5% Et3N-ethyl acetate). The product-containing fractions were concentrated and the product recrystallized from toluene to give 3.66 g, mp 214°-216°.

Workup

  1. temperaturethe mixture warmed at 60° until a homogeneous solution
  2. customwas obtained
  3. temperaturethe temperature of the reaction mixture raised to 120°
  4. temperatureAfter 2 hours it was cooled
  5. customThe organic phase was separated
  6. customdried
  7. concentrationconcentrated
  8. customthe crude product triturated with Et2O
  9. concentrationThe product-containing fractions were concentrated
  10. customthe product recrystallized from toluene
  11. customto give 3.66 g, mp 214°-216°

Sources & evidence

ORD record
ord-224a1e8ad80345f1bc686e01157fbf90
Source dataset
uspto-grants-1991_03
Patent number
US05002955

Reaction notes

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