4-Methoxybenzylamine → 4-Methoxybenzyl isothiocyanate

HRID 2192703Notes

Reaction equation

HRID 2192703 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[C:11](C1NC=CN=1)(C1NC=CN=1)=[S:12]>C(OCC)(=O)C>[N:8]([CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[C:11]=[S:12]

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 11412697Thiocarbonyl diimidazole

Product 1

HCID 1231974-Methoxybenzyl isothiocyanateYield 153.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 0.50 g (3.64 mmols) of the 4-methoxy-benzylamine (M) in 10 mL of ethyl acetate, was added 0.65 g (3.64 mmols) of thiocarbonyl diimidazole (N) portion wise. The resultant mixture was stirred at 50° C. for 10 min. then concentrated. The crude product was then dissolved in 15 mL of dichloromethane and passed through a short pad of silica gel using additional 50 mL of dichloromethane as eluent. Concentration of the filtrate afforded 1.0 g (87%) of (O) as white solid.

Workup

  1. concentrationthen concentrated
  2. dissolutionThe crude product was then dissolved in 15 mL of dichloromethane

Sources & evidence

ORD record
ord-8bc4ae3fb01343b7a606ea5d61c3e8b9
Source dataset
uspto-grants-2012_12
Patent number
US08329736B2

Reaction notes

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