Dimethyl Sulfoxide → HCID 86616319, compound

HRID 641090Notes

Reaction equation

HRID 641090 reaction equation
CS(C)=O.[Br:5][C:6]1[C:7]([Cl:25])=[C:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[C:9]([Cl:16])=[N:10][C:11]=1S(C)(=O)=O.[K].[C:27](#[N:29])C>>[Br:5][C:6]1[C:7]([Cl:25])=[C:8]([C:17]2[C:22]([F:23])=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:24])[C:9]([Cl:16])=[N:10][C:11]=1[C:27]#[N:29]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6342AcetonitrileHCID 5462222PotassiumHCID 86616320HCID 86616320, compound

Product 1

HCID 86616319HCID 86616319, compound

Conditions

Temperature
60 °C

Procedure

At room temperature, a spatula tip (about 10 mg) of crown ether (18-crown-6) and 1 ml of dimethyl sulfoxide were added to 1.65 g (3.8 mmol) of 5-bromo-3-(2-chloro-6-fluorophenyl)-2,4-dichloro-6-methylsulfonylpyridine (Example F) dissolved in 50 ml of acetonitrile, and the mixture was heated to 60° C. Over a period of 6 h, 500 mg (7.6 mmol) of potassium cyamide were then added a little at a time at this temperature. The mixture was stirred at room temperature overnight and chromatographed directly on silica gel using cyclohexane/ethyl acetate. Yield 0.57 g of a solid, m.p. 90° C. 1H-NMR (CDCl3) δ=7.18 (m); 7.40 (m).

Workup

  1. customchromatographed directly on silica gel

Sources & evidence

ORD record
ord-27c49696ae0d460d884c87a1e4e9e84d
Source dataset
uspto-grants-2010_04
Patent number
US07695728B2

Reaction notes

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