Sodium Iodide → HCID 57428859, compound

HRID 507636Notes

Reaction equation

HRID 507636 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-c202751f9c5e47dc81735635260a4078
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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