4-Bromo-1-naphthylamine → 1-Bromo-4-isothiocyanatonaphthalene

HRID 1042638Notes

Reaction equation

HRID 1042638 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[CH:4][CH:3]=1.N1([C:18](N2C=CN=C2)=[S:19])C=CN=C1>ClCCl>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]=[C:18]=[S:19])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 753034-Bromo-1-naphthylamineHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 4593621-Bromo-4-isothiocyanatonaphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-bromo-4-aminonapthalene (2.6 g, 12 mmol) in dichloromethane (45 mL) was added di(1H-imidazol-1-yl)methanethione (2.1 g, 12 mmol). The reaction was allowed to stir for 16 h, at which point the reaction was concentrated to give a gray solid. The solid was slurried in 50% EtOAc/hexanes and filtered through a pad of silica gel, rinsing with 400 mL 50% EtOAc/hexanes. The solution was concentrated to give 1-bromo-4-isothiocyanatonaphthalene as a gray solid, which was used without further purification.

Workup

  1. concentrationwas concentrated
  2. customto give a gray solid
  3. filtrationfiltered through a pad of silica gel
  4. washrinsing with 400 mL 50% EtOAc/hexanes
  5. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-041c880270f0457e9dbb63395c327f26
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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