Sodium Iodide → HCID 57428859, compound

HRID 2267413Notes

Reaction equation

HRID 2267413 reaction equation
BrC1C([C:20]2[S:21][C:22]([Cl:30])=[C:23]([CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])[CH:24]=2)=NC(NCCN2C(C)(C)C(=O)NC2=O)=NC=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:40][CH2:41]CCBr>C(#N)C>[Cl:30][C:22]1[S:21][CH:20]=[CH:24][C:23]=1[CH2:25][CH2:26][N:27]1[CH2:28][CH2:41][CH2:40][CH2:29]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 60204541HCID 60204541, compound

Product 1

HCID 57428859HCID 57428859, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-(2-chlorothiophen-3-yl)ethanamine hydrochloride (3.00 g, 15.1 mmol, prepared as described in Example 329) in acetonitrile (30 mL) was treated with anhydrous potassium carbonate (7.50 g, 54.3 mmol), sodium iodide (5.45 g, 36.4) and 1,4-dibromo-butane (2.2 mL, 18 mmol). The resulting suspension was heated to reflux for 18 h, then cooled, filtered and concentrated to a dark brown oil. Purification by flash chromatography eluting with 1-5% (0.5 M ammonia in MeOH)/dichloromethane afforded the product as a colorless oil (0.45 g, 2.09 mmol, 14% yield). MS (M+H)+ 216.

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux for 18 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationconcentrated to a dark brown oil
  6. customPurification by flash chromatography
  7. washeluting with 1-5% (0.5 M ammonia in MeOH)/dichloromethane

Sources & evidence

ORD record
ord-54e1fb2f5b934f46b9b3535ac7300cd7
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…