Diisopropylethylamine → HCID 178516947, compound

HRID 852988Notes

Reaction equation

HRID 852988 reaction equation
Cl.[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH2:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:12]1[CH2:18][C:16](=[O:17])[NH:15][C:13]1=S.C(N(CC)C(C)C)(C)C>C(#N)C>[C:2]1([C@@H:8]2[CH2:10][C@H:9]2[NH:11][C:13]2[S:12][CH2:18][C:16](=[O:17])[N:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1201546RhodanineHCID 2723716Tranylcypromine hydrochloride

Product 1

HCID 178516947HCID 178516947, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of (1R,2S)-2-phenyl-cyclopropylamine hydrochloride (0.85 g, 5 mmol) and rhodanine (2-thio-4-thiazolin-4-one) (0.68 g, 5 mmol) in acetonitrile (20 mL) was added DIEA (N,N-diisopropylethylamine) (2.61 mL, 15 mmol) at room temperature. Then, this solution was cooled to 0° C. and mercuric chloride (1.35 g, 5 mmol) was added in two portions within a period of 10 min. After addition, the suspension was allowed to warm to room temperature and stirred for 2 days. The resulting black solids were filtered through a plug of celite and washed with ethyl acetate (500 mL). The filtrates were removed under the vacuum and the crude residue was diluted with water (100 mL) and ethyl acetate (100 mL). The two layers were separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The combined organic extracts were washed with brine solution and dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent under the vacuum gave the crude residue which was purified by using a Biotage silica gel column chromatography to obtain 0.474 g (42% yield) of 2-((1R,2S)-2-phenyl-cyclopropylamino)-thiazol-4-one as a white amorphous solid: EI-HRMS m/e calcd for C12H12N2OS (M+) 232.0670, found 232.0665.

Workup

  1. additionAfter addition
  2. temperatureto warm to room temperature
  3. filtrationThe resulting black solids were filtered through a plug of celite
  4. washwashed with ethyl acetate (500 mL)
  5. customThe filtrates were removed under the vacuum
  6. additionthe crude residue was diluted with water (100 mL) and ethyl acetate (100 mL)
  7. customThe two layers were separated
  8. extractionthe aqueous layer was extracted with ethyl acetate (2×100 mL)
  9. washThe combined organic extracts were washed with brine solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationFiltration of the drying agent and removal of the solvent under the vacuum
  12. customgave the crude residue which
  13. customwas purified

Sources & evidence

ORD record
ord-d004fa0eb0c04adfab033f3da2788239
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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