Ammonia → 4-(4-Methylthiophenoxy)benzylamine

HRID 1591109Notes

Reaction equation

HRID 1591109 reaction equation
[NH3:1].[CH3:2][C:3]1[CH:17]=[CH:16][C:6]([S:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.O>CO>[CH3:2][C:3]1[CH:17]=[CH:16][C:6]([S:7][C:8]2[CH:15]=[CH:14][C:11]([CH2:12][NH2:1])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 1317178844-(4-Methylthiophenoxy)benzylbromide

Product 1

HCID 435288314-(4-Methylthiophenoxy)benzylamineYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred mixture of 28% aq NH3 (40 ml) and methanol (200 ml) was added dropwise a solution (20 ml) of 4-(4-methylthiophenoxy)benzylbromide (5.00 g, 16.2 mM) in methanol at room temperature, and the mixture was stirred for 4 days at the same temperature. To the mixture was added water (100 ml), and the mixture was concentrated in vacuo. The residue was diluted with chloroform, and the mixture was washed with water and brine, dried with sodium sulfate, and concentrated in vacuo. The residue was chromatographed over alumina to give 4-(4-methylthiophenoxy)benzylamine (2.11 g, 53%) as colorless crystals, m.p. 61.8° C.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted with chloroform
  3. washthe mixture was washed with water and brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed over alumina

Sources & evidence

ORD record
ord-55cf9224a7dd44b796f9a12d7042ff05
Source dataset
uspto-grants-1993_04
Patent number
US05206259

Reaction notes

Loading…