Methane → HCID 58372871, compound

HRID 888471Notes

Reaction equation

HRID 888471 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][C:16]=2[CH2:24][S:25][CH2:26][C:27]([F:30])([F:29])[F:28])[CH:7]=1)[CH3:2].CN(C)N.C>CCO>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][C:16]=2[CH2:24][S:25][CH2:26][C:27]([F:28])([F:29])[F:30])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 297MethaneHCID 59761,1-DimethylhydrazineHCID 58372816HCID 58372816, compound

Product 1

HCID 58372871HCID 58372871, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of {4-methoxy-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid ethyl ester (1.46 g, 3.18 mmol), ferric chloride (0.026 g, 0.16 mmol), 1,1-dimethylhydrazine (1.69 mL, 22.27 mmol), and DARCO (0.300 g) in EtOH (30 mL) was stirred overnight at 65° C. The mixture was partitioned between EtOAc and H2O and extracted three times with EtOAc. The combined organic layers were washed with H2O and brine, and then dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (EtOAc in hexanes gradient) to give the title compound.

Workup

  1. customThe mixture was partitioned between EtOAc and H2O
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layers were washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (EtOAc in hexanes gradient)

Sources & evidence

ORD record
ord-d26be22312da46f89b13bf449f1485a3
Source dataset
uspto-grants-2012_08
Patent number
US08247602B2

Reaction notes

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