1-Naphthyl Isothiocyanate → 1-Naphthalen-1-yl-3-[5-(3-nitro-phenoxy)-pentyl]-thiourea

HRID 599181Notes

Reaction equation

HRID 599181 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])([O-:3])=[O:2].[C:17]1([N:27]=[C:28]=[S:29])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1>ClCCl>[C:17]1([NH:27][C:28]([NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:6]2[CH:14]=[CH:15][CH:16]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[S:29])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 110801-Naphthyl IsothiocyanateHCID 690096135-(3-Nitro-phenoxy)-pentylamine

Product 1

HCID 866252701-Naphthalen-1-yl-3-[5-(3-nitro-phenoxy)-pentyl]-thioureaYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(3-nitro-phenoxy)-pentylamine (867 mg, 3.87 mmol) in dichloromethane (5 mL) was added 1-naphthyl isothiocyanate (788 mg, 4.26 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight. After removal of the solvent, the residue was purified by silica gel column chromatography to give 1-naphthalen-1-yl-3-[5-(3-nitro-phenoxy) -pentyl]-thiourea (1.3 g, 3.18 mmol, 82%) as a yellow gel.

Workup

  1. customAfter removal of the solvent
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0a8a51399d4f4cf49a2c11518ef092c1
Source dataset
uspto-grants-2011_03
Patent number
US07897764B2

Reaction notes

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