Phenol → 3-Phenoxy-4-phenyl-1,2,5-thiadiazole

HRID 1583969Notes

Reaction equation

Cl[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][S:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[O:25]([C:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][S:4][N:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Under a dry nitrogen atmosphere 4.1 g (0.0021 mole) of 3-chloro-4-phenyl-1,2,5-thiadiazole was added to a stirred mixture of 3.73 g (0.0027 mole) of potassium carbonate and 2.4 g (0.0026 mole) of phenol in 50 ml of N,N-dimethylformamide. After complete addition the mixture was heated at 120° C. for 21 hours. The mixture was cooled, poured into 400 ml of ice water and the mixture extracted with diethyl ether. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was evaporated under reduced pressure to leave a residue. The residue was purified by column chromatography on silica gel, eluted with n-hexane:methylene chloride (1:1) to yield 4.8 g of 3-phenoxy-4-phenyl-1,2,5-thiadiazole, Compound 38 of Table I.

Workup

additionAfter complete addition the mixture
temperatureThe mixture was cooled
extractionthe mixture extracted with diethyl ether
dry with materialThe extract was dried over anhydrous magnesium sulfate
filtrationfiltered
customThe filtrate was evaporated under reduced pressure
customto leave a residue
customThe residue was purified by column chromatography on silica gel
washeluted with n-hexane:methylene chloride (1:1)

Sources & evidence

ORD record: ord-9c219fea8f8f43599f080f6e7d5c88dc
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04555521

Reaction notes

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