Thiophosgene → 4-Isothiocyanato-1-naphthonitrile
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
Product 1
Reagents, catalysts & solvents 2
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 (200 mL) 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
- customThe layers were separated
- concentrationthe organic layer concentrated
Sources & evidence
- ORD record
- ord-ee4c36772a5e4b93900d86847385c95d
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193234B2
Reaction notes
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