Benzylamine → HCID 178435254, compound

HRID 1354574Notes

Reaction equation

HRID 1354574 reaction equation
Br[CH2:2][C:3]([C:5]1([CH2:15][CH3:16])[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:14])[CH:11]=2)[CH2:6]1)=O.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[S-:25][C:26]#[N:27].[K+]>C(O)C>[CH2:17]([N:24]1[C:3]([C:5]2([CH2:15][CH3:16])[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([F:14])[CH:11]=3)[CH2:6]2)=[CH:2][N:27]=[C:26]1[SH:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7504Benzylamine2×HCID 516872Potassium thiocyanateHCID 11961662HCID 11961662, compound

Product 1

HCID 178435254HCID 178435254, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.62 g of 2-bromo-1-(2-ethyl-5-fluoro-indan-2-yl)-ethanone was dissolved in 25 ml of ethanol in a glass round-bottomed flask equipped with a mechanical stirrer, a thermometer and a dropping funnel. The reaction mixture was heated to reflux temperature while stirring. 0.366 g of benzylamine dissolved in 5 ml ethanol was added slowly in a drop-wise fashion to the solution. After the addition of benzylamine the mixture was refluxed for one hour. 0.330 g of potassium thiocyanate was added portionwise during 30 minutes and the reaction mixture was refluxed for 2 hours. The reaction mixture was evaporated to dryness before 150 ml ethyl acetate was added and the solution was washed with water. The organic phase was dried over Na2SO4, filtered and evaporated providing 1.13 g of 1-benzyl-5-(2-ethyl-5-fluro-indan-2-yl)-imidazole-2-thiol (yield 31%). The analytical sample was purified using TLC-plates. The purity was measured by HPLC: 62%. Normally the crude product was used in the following step.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux temperature
  4. additionwas added slowly in a drop-wise fashion to the solution
  5. temperaturewas refluxed for one hour
  6. temperaturethe reaction mixture was refluxed for 2 hours
  7. customThe reaction mixture was evaporated to dryness before 150 ml ethyl acetate
  8. additionwas added
  9. washthe solution was washed with water
  10. dry with materialThe organic phase was dried over Na2SO4
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-05161de800304d6daf9c952ffa8fe2b1
Source dataset
uspto-grants-2007_05
Patent number
US07223871B2

Reaction notes

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