Iodoethane → HCID 66671971, compound

HRID 1698393Notes

Reaction equation

HRID 1698393 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7](N)=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[CH2:15](I)[CH3:16].[Cl-].[NH4+:19]>CS(C)=O>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:16][CH2:15][NH2:19])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 119590004-bromo-2-tert-butylphenylamine

Product 1

HCID 66671971HCID 66671971, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
0 °C

Procedure

2.7 g (68 mmol) of sodium hydride are suspended in 250 ml of DMSO, under a stream of nitrogen. 7 g (31 mmol) of 4-bromo-2-tert-butylphenylamine, diluted in 10 ml of DMSO, are added to the reaction medium cooled to 0° C. After stirring at ambient temperature for 30 minutes, 5.4 ml (68 mmol) of ethyl iodide are added slowly. The pale-yellow-coloured mixture is stirred overnight at ambient temperature and then poured into a saturated solution of ammonium chloride and extracted twice with ethyl acetate. The organic phase is dried and then concentrated under vacuum. 5 g of (4-bromo-2-tert-butylphenyl)ethylamine are obtained in the form of a yellow oil (yield=65%).

Workup

  1. additionare added to the reaction medium
  2. stirringThe pale-yellow-coloured mixture is stirred overnight at ambient temperature
  3. extractionextracted twice with ethyl acetate
  4. customThe organic phase is dried
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7e2c5c10d2da4272bbe575cea0f49ca8
Source dataset
uspto-grants-2012_04
Patent number
US08163952B2

Reaction notes

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