Thiophosgene → 4-Isothiocyanato-1-naphthonitrile

HRID 1799137Notes

Reaction equation

HRID 1799137 reaction equation
[C:1](Cl)(Cl)=[S:2].[NH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]#[N:17])=[CH:8][CH:7]=1>ClCCl.C([O-])(O)=O.[Na+]>[N:5]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16]#[N:17])=[CH:8][CH:7]=1)=[C:1]=[S:2]

Participants

5

Reactant 2

HCID 10040ThiophosgeneHCID 428284-Amino-1-naphthalenecarbonitrile

Product 1

HCID 183160684-Isothiocyanato-1-naphthonitrileYield 93.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Thiophosgene (9.1 mL, 118.9 mmol) was added to a stirring slurry of 4-amino-1-naphthalenecarbonitrile (10 g, 59.45 mmol) in dichloromethane (200mL) and saturated aqueous NaHCO3 solution (200 mL) at 0° C., and the mixture stirred for 3 days at room temp. The layers were separated and the organic layer concentrated to provide 4-isothiocyanato-1-naphthonitrile as a tan solid (11.64 g, 93%).

Workup

  1. customThe layers were separated
  2. concentrationthe organic layer concentrated

Sources & evidence

ORD record
ord-c523b29e6f174f00990ccfd527d88a85
Source dataset
uspto-grants-2013_01
Patent number
US08344012B2

Reaction notes

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