Thiourea → HCID 86634303, compound

HRID 1446690Notes

Reaction equation

HRID 1446690 reaction equation
Br[CH:2]([CH:12]([CH3:14])[CH3:13])[C:3](=O)[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1)=[O:5].[NH2:15][C:16]([NH2:18])=[S:17]>C(O)C>[NH2:18][C:16]1[S:17][C:2]([CH:12]([CH3:14])[CH3:13])=[C:3]([C:4]([N:6]2[CH2:10][CH2:9][CH2:8][CH2:7]2)=[O:5])[N:15]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86634304HCID 86634304, compound

Product 1

HCID 86634303HCID 86634303, compoundYield 1,467.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add 3-bromo-4-methyl-1-pyrrolidin-1-yl-pentane-1,2-dione (3.0 g, 11.44 mmol, 1.0 eq.) to the solution of thiourea (1.31 mmol, 1.5 eq.) in ethanol (40 mL). Stir the reaction mixture at reflux for overnight. Concentrate in vacuo. Add dichloromethane (200 mL). Wash the organic layer with sodium bicarbonate (sat. 2×30 mL), aqueous saturated sodium chloride (2×20 mL) and water (2×30 mL). Dry the organic phase over MgSO4 and filter the drying reagent off. Concentrate in vacuo. Purify by column chromatography (0%→5% ethyl acetae in dichloromethane) to afford product (4.60 g, 66%). MS(ES), m/z 240 (M+1).

Workup

  1. temperatureat reflux for overnight
  2. concentrationConcentrate in vacuo
  3. washWash the organic layer with sodium bicarbonate (sat. 2×30 mL), aqueous saturated sodium chloride (2×20 mL) and water (2×30 mL)
  4. dry with materialDry the organic phase over MgSO4
  5. filtrationfilter the drying reagent off
  6. concentrationConcentrate in vacuo
  7. customPurify by column chromatography (0%→5% ethyl acetae in dichloromethane)

Sources & evidence

ORD record
ord-f069cc2541e04d5ca4b951f36d22ce77
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

Loading…