Thiophenol → HCID 136354596, compound

HRID 1283411Notes

Reaction equation

HRID 1283411 reaction equation
[C:1]1([N:7]2[C:11]([S:12][C:13]3[C:14](=[O:28])[C:15]([C:20]([CH3:27])([CH3:26])[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:16][C:17](=[O:19])[CH:18]=3)=[N:10][N:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:29]1([SH:35])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CO>[C:1]1([N:7]2[C:11]([S:12][C:13]3[C:18]([S:35][C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:17]([OH:19])[CH:16]=[C:15]([C:20]([CH3:27])([CH3:26])[CH2:21][C:22]([CH3:23])([CH3:25])[CH3:24])[C:14]=3[OH:28])=[N:10][N:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7969ThiophenolHCID 21518032HCID 21518032, compound

Product 1

HCID 136354596HCID 136354596, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

15g of 2-(1-phenyl-5-tetrazolylthio)-6-(1,1,3,3-tetramethylbutyl)-p-benzoquinone was added to 150ml of methanol and the mixture was cooled to 0°C while stirring. Then a solution of 4.5g of thiophenol in 25ml of methanol was added dropwise to this mixture. After the addition, the mixture was stirred at 0°C for 3 hours. The resulting crystals were separated by filtration and recrystallized from a solvent mixture of n-hexane and ethyl acetate (n-hexane/ethyl acetate = 5/1 by volume). Thus 7.5g of 2-(1-phenyl-5-tetrazolylthio)-3-phenylthio-6-(1,1,3,3-tetramethylbutyl)-hydroquinone having a melting point of 147°C was obtained.

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred at 0°C for 3 hours
  3. customThe resulting crystals were separated by filtration
  4. customrecrystallized from a solvent mixture of n-hexane and ethyl acetate (n-hexane/ethyl acetate = 5/1 by volume)

Sources & evidence

ORD record
ord-42b2c56145794b0f86b28a481405fd16
Source dataset
uspto-grants-1976_08
Patent number
US03975395

Reaction notes

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