Sodium Hydroxide → HCID 59475100, compound

HRID 450704Notes

Reaction equation

HRID 450704 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][CH:8]([NH2:10])[CH3:9].[Br:11]Br.C(OC)(C)(C)C.[OH-].[Na+]>C(O)(=O)C>[Br:11][C:5]1[S:4][C:3]([CH2:7][CH:8]([NH2:10])[CH3:9])=[C:2]([Cl:1])[CH:6]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 24408BromineHCID 49892HCID 49892, compound

Product 1

HCID 59475100HCID 59475100, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

In a sulfonation flask 5 g (0.028 mol) 2-(3-chlorothiphen-2-yl)-1-methylethylamine is dissolved in 70 ml of acetic acid. The mixture is then cooled to 15° C. and 4.8 g (0.30 m) of bromine is added under stirring (internal temperature 15-17° C.). After warming up to rt, the mixture is stirred for 16 hours. Then the mixture is poured to a mixture of tert. butylmethylether (ca. 250 ml) and 2N sodiumhydroxide. The final pH is 11. After washing with brine, drying with sodium sulphate and evaporation of the solvent the crude material is obtained. Purification is achieved by column chromatography over silicagel (eluent: tert. butylmethylether/EtOH 10:1). Yield: 5.4 g (75% of theory) of a colourless oil (1H-NMR: 1.18/d/3H, 2.68-2.87/m (diasterotopic protons)/2H, 3.2/m/1H, 6.87/s/1H).

Workup

  1. temperatureAfter warming up to rt
  2. stirringthe mixture is stirred for 16 hours
  3. washAfter washing with brine
  4. dry with materialdrying with sodium sulphate and evaporation of the solvent the crude material
  5. customis obtained
  6. customPurification

Sources & evidence

ORD record
ord-ca82a941939f449c8f71b6ea499d5146
Source dataset
uspto-grants-2013_07
Patent number
US08486986B2

Reaction notes

Loading…