Methyl Ethyl Ketone → HCID 86744960, compound

HRID 2253626Notes

Reaction equation

HRID 2253626 reaction equation
[S:1]1CCC(=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+].[CH3:19][C:20](=O)[CH2:21]C>[Cl-].[Cl-].[Zn+2]>[NH:11]1[C:10]2[C:9]3=[C:8]([NH2:16])[S:1][CH2:2][CH:3]=[C:15]3[CH:14]=[CH:13][C:12]=2[CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 14798Sodium HydroxideHCID 66173Tetrahydrothiopyran-4-oneHCID 729132-Aminobenzonitrile

Product 1

HCID 86744960HCID 86744960, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
60 °C

Procedure

Tetrahydrothiopyran-4-one (10.0 g) was mixed with anthranilonitrile (5.08 g) and the mixture warmed at 60° C. 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° C. After two (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, m.p. 214°-216° C.

Workup

  1. customwas obtained
  2. temperaturethe temperature of the reaction mixture raised to 120° C
  3. customThe organic phase was separated
  4. customdried
  5. concentrationconcentrated
  6. customthe crude product triturated with Et2O
  7. concentrationThe product-containing fractions were concentrated
  8. customthe product recrystallized from toluene
  9. customto give 3.66 g, m.p. 214°-216° C.

Sources & evidence

ORD record
ord-87554f0d0b28445c938163213fd29e07
Source dataset
uspto-grants-1993_08
Patent number
US05232927

Reaction notes

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