Ethyl isothiocyanate → HCID 22386883, compound

HRID 1072525Notes

Reaction equation

HRID 1072525 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.[N:21]([CH2:24][CH3:25])=[C:22]=[S:23]>O1CCCC1>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:22]([NH:21][CH2:24][CH3:25])=[S:23])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 10966Ethyl isothiocyanateHCID 99443944-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline2×

Product 1

HCID 22386883HCID 22386883, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydro-isoquinolin-4-yl)-phenylamine (50 mg, example 17, intermediate 1) was dissolved in tetrahydrofurane (4 ml) and isothiocyanato-ethane (14 mg) was added to the stirred solution. After 2 h at reflux temperature the solution was concentrated and the residue kept for 2 h at 85° C. The crude product was purified by preparative HPLC. The product containing fractions were combined and the acetonitrile was removed in vaccuo. After addition of potassium carbonate the aqueous phase was extracted with ethyl acetate. The organic layer was separated, dried (magnesium sulphate), filtered and concentrated in vaccuo. The residue was dissolved in water/2N hydrochloric acid and freeze dried to give 33 mg of the title compound.

Workup

  1. temperatureAfter 2 h at reflux temperature the solution
  2. concentrationwas concentrated
  3. customThe crude product was purified by preparative HPLC
  4. additionThe product containing fractions
  5. customthe acetonitrile was removed in vaccuo
  6. additionAfter addition of potassium carbonate the aqueous phase
  7. extractionwas extracted with ethyl acetate
  8. customThe organic layer was separated
  9. dry with materialdried (magnesium sulphate)
  10. filtrationfiltered
  11. concentrationconcentrated in vaccuo
  12. dissolutionThe residue was dissolved in water/2N hydrochloric acid
  13. customfreeze dried

Sources & evidence

ORD record
ord-675079c8f2d249aaace796ee6eeae7fb
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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