Sodium Carbonate → HCID 15572245, compound

HRID 2286588Notes

Reaction equation

HRID 2286588 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11](C=O)[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:30][C:31]([F:35])([F:34])[S:32]Cl>CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([S:32][C:31]([F:35])([F:34])[F:30])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 67900Methanesulfenyl chloride, trifluoro-3×HCID 15572341HCID 15572341, compound

Product 1

HCID 15572245HCID 15572245, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 1.5 g (5 m mole) of 4,5-bis(4-methoxyphenyl)pyrrole-2-carboxaldehyde and 1.3 g sodium carbonate in 10 ml ether/10 ml THF at -78° was added 0.8 g of trifluoromethanesulfenyl chloride. The mixture was allowed to warm to room temperature with a dry-ice condenser attached to keep the trifluoromethanesulfenyl chloride from escaping. Excess trifluoromethanesulfenyl chloride was added and the mixture was stirred overnight at room temperature. The mixture was filtered and the filtrate concentrated by rotary evaporation. The residue was purified by chromatography on 300 g Silic AR CC-7, eluting with toluene, to give 0.75 g (39%) of product, identical to that obtained by Method A.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated by rotary evaporation
  3. customThe residue was purified by chromatography on 300 g Silic AR CC-7
  4. washeluting with toluene

Sources & evidence

ORD record
ord-5c00b0e1e6294f7e9334cb74a494edc1
Source dataset
uspto-grants-1981_05
Patent number
US04267184

Reaction notes

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