Carbon Disulfide → 5-[2-(2,6-Dichloro-3-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazole-2-thiol

HRID 2211168Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][NH2:16])=[O:14].[C:21](=S)=[S:22].[OH-].[K+]>CO>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]1[O:14][C:21](=[S:22])[NH:16][N:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-[(2,6-Dichloro-3-methylphenyl)amino]-benzoic acid, hydrazide (1.172 g, 3.78 mmol) is dissolved in 20 ml of methanol, and the solution is cooled to 0° C. Carbon disulfide (520 μl, 8.82 mmol) is added, followed by potassium hydroxide (266.0 mg, 4.03 mmol). The solution is heated at reflux for seven hours and allowed to cool to room temperature overnight. The solution is concentrated in vacuo and the residue dissolved in water. The aqueous solution is acidified with 1N hydrochloric acid and the resulting solids extracted into a 1:1 mixture of ether and ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is chromatographed, eluting with hexane:ethyl acetate (2:1) providing 864.0 mg (65%) of product, mp 257°-259° C.

Workup

temperatureThe solution is heated
temperatureat reflux for seven hours
temperatureto cool to room temperature overnight
concentrationThe solution is concentrated in vacuo
dissolutionthe residue dissolved in water
extractionthe resulting solids extracted into a 1:1 mixture of ether and ethyl acetate
dry with materialThe organic layer is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue is chromatographed
washeluting with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record: ord-e721b36464ef49c9852cef7ec3ba5a01
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05462952

Reaction notes

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