HCID 12090421, compound → HCID 12090422, compound

HRID 1058551Notes

Reaction equation

HRID 1058551 reaction equation
[CH2:1]([S:8][C:9]1[C:10]([O:21][CH3:22])=[C:11](C(O)=O)[S:12][C:13]=1[C:14]([F:17])([F:16])[F:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH2:1]([S:8][C:9]1[C:10]([O:21][CH3:22])=[CH:11][S:12][C:13]=1[C:14]([F:17])([F:16])[F:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12090421HCID 12090421, compound

Product 1

HCID 12090422HCID 12090422, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3.6 g of 4-benzylthio-3-methoxy-5-trifluoromethyl-2-thiophenecarboxylic acid and 0.85 g of copper powder in 50 mL of quinoline was heated to 150° C. for 15 min. The mixture was cooled and partitioned with ether and aqueous HCl. The organic phase was separated, dried over MgSO4, filtered, concentrated and purified by column chromatography to give 2.2 g (71%) of an amber oil. 1H NMR (300 MHz, CDCl3): δ 7.2 (m, 5H); 6.4 (s, 1H); 4.1 (s, 2H); 3.8 (s, 3H). Anal. Calc'd for C13H11F3OS2: C, 51.30; H, 3.64; S, 21.07. Found: C, 51.13; H, 3.54; S, 21.02.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned with ether and aqueous HCl
  3. customThe organic phase was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-44af9c23c95d417497a55b10069fc408
Source dataset
uspto-grants-2003_02
Patent number
US06518222B2

Reaction notes

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