Ethyl xanthate → 2-Sulfanylidene-2,3-dihydro-1,3-benzothiazole-6-carbonitrile

HRID 1865514Notes

Reaction equation

HRID 1865514 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1Cl.C(O[C:14]([SH:16])=[S:15])C.[K]>CN(C=O)C>[SH:16][C:14]1[S:15][C:3]2[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[CH:9][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 8823Ethyl xanthateHCID 5198964-Amino-3-chlorobenzonitrileHCID 5462222Potassium

Product 1

HCID 1785095042-Sulfanylidene-2,3-dihydro-1,3-benzothiazole-6-carbonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared using the method of example 239, starting with 4-amino-3-chloro-benzonitrile (Lancaster, 5.0 g, 32.7 mmol), O-ethylxanthic acid, potassium salt (Lancaster, 11.8 g, 73.7 mmol) in DMF (40 mL). The mercaptobenzothiazole (241) (6.1 g, 97%) was obtained as a pale brown solid.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-68ec1b084f0f4e6ca43dfc9e66b850dd
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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