Thiophene → HCID 14738653, compound

HRID 1757602Notes

Reaction equation

HRID 1757602 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[F:20][P-:21]([F:26])([F:25])([F:24])([F:23])[F:22].[K+]>O>[F:20][P-:21]([F:26])([F:25])([F:24])([F:23])[F:22].[C:1]1([S+:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:16]2[S:15][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8030ThiopheneHCID 13679Diphenyl sulfoxideHCID 23688904Potassium hexafluorophosphate

Product 1

HCID 14738653HCID 14738653, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

There was added 20 ml of the PP/MSA solution to a mixture of 10.1 grams (0.05 mole) of diphenylsulfoxide and 4.2 grams (0.05 mole) of thiophene. The resulting mixture exothermed to 50° C. and became viscous and purple in color. After 0.5 hours, the blue reaction mixture was poured into 200 ml of water. A very dark colored solution was obtained. It was added to the solution, 9.2 grams (0.05 mole) of potassium hexafluorophosphate. A dark colored solid was obtained. The solid was isolated by decantation and washed several times with fresh water and thenfiltered. The solid was dissolved in dichloromethane and passed through a column of neutral alumina. A pale yellow crystalline solid was obtained upon evaporation of the solvent. It was recovered, 10.6 grams for a 51.2% yield of diphenyl (2-thiophenyl) sulfonium hexafluorophosphate having a melting point of 177°-173° C. Elemental analysis showed; Calculated: % carbon 46.30; % hydrogen 3.14; % sulfur 15.46; Found: % carbon 46.80; % hydrogen 3.12; % sulfur 15.75.

Workup

  1. additionThere was added 20 ml of the PP/MSA solution
  2. customexothermed to 50° C.
  3. customthe blue reaction mixture
  4. customA very dark colored solution was obtained
  5. customA dark colored solid was obtained
  6. customThe solid was isolated by decantation
  7. washwashed several times with fresh water
  8. dissolutionThe solid was dissolved in dichloromethane
  9. customA pale yellow crystalline solid was obtained upon evaporation of the solvent
  10. customIt was recovered

Sources & evidence

ORD record
ord-7cbd7f47791c4f1f8f97de2c6d910fc7
Source dataset
uspto-grants-1995_08
Patent number
US05446172

Reaction notes

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