1,1'-Thiocarbonyldiimidazole → HCID 59749560, compound

HRID 747276Notes

Reaction equation

HRID 747276 reaction equation
[N:1]1[C:10]2[C:5](=[C:6]([CH:11]([CH3:16])[CH:12]([NH2:15])[CH2:13][NH2:14])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:17](N1C=CN=C1)(N1C=CN=C1)=[S:18]>C(Cl)Cl.C(Cl)(Cl)Cl.O>[N:1]1[C:10]2[C:5](=[C:6]([CH:11]([CH:12]3[CH2:13][NH:14][C:17](=[S:18])[NH:15]3)[CH3:16])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 59749539HCID 59749539, compound2×

Product 1

HCID 59749560HCID 59749560, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-Quinolin-5-yl-butane-1,2-diamine (Intermediate E3) (1.8 g, 8.35 mmol) in CH2Cl2 (20 mL) was treated with a solution of 1,1′-thiocarbonyldiimidazole (1.52 g, 8.54 mmol) in CH2Cl2 (40 mL) at 0° C. for 1 h. The mixture was diluted with chloroform (40 mL) and water (60 mL). The aqueous layer was extracted with chloroform (3×30 mL) and CH2Cl2 (6×30 mL). The organic solution was dried over MgSO4, filtered and evaporated to give a residue. The material was purified by chromatography on SiO2 with 3% NH3-MeOH:CH2Cl2 to give 4-(1-quinolin-5-yl-ethyl)-imidazolidine-2-thione (Intermediate E4) 2 g (93%).

Workup

  1. extractionThe aqueous layer was extracted with chloroform (3×30 mL) and CH2Cl2 (6×30 mL)
  2. dry with materialThe organic solution was dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customto give a residue
  6. customThe material was purified by chromatography on SiO2 with 3% NH3-MeOH

Sources & evidence

ORD record
ord-d9215370fa1e445692c29e37ae7683cf
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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