Hydrochloric Acid → 1-Methyl-3,5-diphenyl-4-(phenylsulfanyl)-1H-pyrazole

HRID 1439137Notes

Reaction equation

HRID 1439137 reaction equation
Br[C:2]1[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:4][N:5]([CH3:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C2C(=CC=CC=2)C=CC=1.Cl>N1C=CC=CC=1>[CH3:13][N:5]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]([S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 7969ThiophenolHCID 213980514-Bromo-1-methyl-3,5-diphenyl-1H-pyrazole

Product 1

HCID 213980551-Methyl-3,5-diphenyl-4-(phenylsulfanyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4-bromo-1-methyl-3,5-diphenylpyrazole (21.84 g, 0.07 mole), copper(1)salt of benzenethiol (14.67 g, 0.085 mole), pyridine (10 ml) and quinoline (100 ml) is stirred and heated at 175° C to 185° C (reflux) for 8 hours. The reaction mixture is allowed to stand overnight at room temperature. The mixture is poured into dilute hydrochloride acid and extracted with benzene. The benzene layer is separated and stripped in vacuo to give a brown syrup. The syrup is extracted with a hot mixture of n-hexane and n-heptane and filtered. The cooled filtrate yields a gray colored solid m.p. 109° C to 110° C. Recrystallization from n-hexane affords white crystals 17.35 g (74.5%), m.p. 109° C to 110° C.

Workup

  1. temperatureheated at 175° C to 185° C
  2. temperature(reflux) for 8 hours
  3. extractionextracted with benzene
  4. customThe benzene layer is separated
  5. customto give a brown syrup
  6. extractionThe syrup is extracted with a hot mixture of n-hexane and n-heptane
  7. filtrationfiltered

Sources & evidence

ORD record
ord-8ae2f3553247476d99f5b2e2676572e8
Source dataset
uspto-grants-1977_11
Patent number
US04058391

Reaction notes

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