Sodium Carbonate → HCID 15572244, compound

HRID 2286585Notes

Reaction equation

HRID 2286585 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:24][C:25]([F:29])([F:28])[S:26]Cl>CCOCC>[C:12]1([C:11]2[CH:10]=[C:9]([S:26][C:25]([F:29])([F:28])[F:24])[NH:8][C:7]=2[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67900Methanesulfenyl chloride, trifluoro-HCID 10104838HCID 10104838, compound

Product 1

HCID 15572244HCID 15572244, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In glassware flamed out, under nitrogen, and fitted with a dry ice condenser, were placed 11 g (0.05 mole) 2,3-diphenylpyrrole, 6.4 g (0.06 mole) anhydrous sodium carbonate and 200 ml ether. The mixture was chilled to -30° and 7.6 g (0.055 mole) trifluoromethanesulfenyl chloride was added as a gas from a tared trap. The reaction was stirred at -30° one-half hour, then allowed to warm to room temperature for two hours. The inorganic salts were removed by filtration and the ether filtrate was concentrated. The residue was chromatographed on 300 g Silic AR CC-7 eluting with hexane containing 5-10% toluene. The product was obtained as a white solid, 15.4 g (96%), m.p. 58°-9°.

Workup

  1. temperatureIn glassware flamed out, under nitrogen
  2. customfitted with a dry ice condenser
  3. temperatureThe mixture was chilled to -30°
  4. customThe inorganic salts were removed by filtration
  5. concentrationthe ether filtrate was concentrated
  6. customThe residue was chromatographed on 300 g Silic AR CC-7 eluting with hexane containing 5-10% toluene
  7. customThe product was obtained as a white solid, 15.4 g (96%), m.p. 58°-9°

Sources & evidence

ORD record
ord-fe8d162dc4584a4a8399df9a2dcf4924
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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