Acetaldehyde, 2,2-dimethoxy- → HCID 19699494, compound

HRID 863065Notes

Reaction equation

HRID 863065 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C@H:6]([NH2:13])[CH2:7]2.CO[CH:16](OC)[CH:17]=O.[S-:21][C:22]#[N:23].[K+]>C(O)C.[Pd].Cl>[F:1][C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]([N:13]1[CH:16]=[CH:17][NH:23][C:22]1=[S:21])[CH2:7]2

Participants

7

Reactant 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 516872Potassium thiocyanateHCID 15290005(2S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 19699494HCID 19699494, compoundYield 42.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent2×

Procedure

A mixture of (S)-5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-ylamine (2.05 g, 11.2 mmol), prepared as in Example 8, and dimethoxyacetaldehyde (1.73 g, 13.1 mmol) in 50 mL of ethanol was hydrogenated over 10% palladium on carbon (500 mg) for 18 hours. The mixture was filtered and concentrated by evaporation. The residue was combined with potassium thiocyanate (1.57 g, 16.2 mmol) in 30 mL of 1N hydrochloric acid and 20 mL of ethanol and the mixture was heated at 70°-80° C. for 18 hours. The mixture was cooled in an ice bath giving a crystalline material which was isolated by filtration. Recrystallization from ethyl acetate/hexane gave 1-(5,7-difluoro-1,2,3,4-tetrahydronaphthalen-2-yl)-1,3-dihydroimidazole-2-thione (1.27 g, 4.76 mmol), m.p. 250°-251° C.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated by evaporation
  3. temperaturethe mixture was heated at 70°-80° C. for 18 hours
  4. temperatureThe mixture was cooled in an ice bath
  5. customgiving a crystalline material which
  6. customwas isolated by filtration
  7. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5d1f58fc539846cfb6c8f5cec65f64dd
Source dataset
uspto-grants-1998_02
Patent number
US05719280

Reaction notes

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