o-Iodonitrobenzene → HCID 18720590, compound

HRID 841198Notes

Reaction equation

HRID 841198 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([SH:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:14])[F:13].I[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N+:26]([O-:28])=[O:27].C[O-].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([S:8][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N+:26]([O-:28])=[O:27])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:18])[C@:11]([OH:17])([CH3:16])[C:12]([F:15])([F:13])[F:14]

Participants

6

Reactant 3

HCID 69115o-IodonitrobenzeneHCID 10942334Sodium MethoxideHCID 54333950HCID 54333950, compound

Product 1

HCID 18720590HCID 18720590, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of (R)-N-(2-chloro-4-mercaptophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (0.1 g), 1-iodo-2-nitrobenzene (0.086 g), sodium methoxide (0.021 g), and cuprous chloride (0.014 g) in DMF (1 ml) was stirred and heated to 135° C. for 2.5 hours then allowed to cool to room temperature. The reaction mixture was diluted with water (5 ml) and poured onto a Varian Chem Elut column. When the liquid had been adsorbed the column was eluted with ethyl acetate and the eluate was concentrated by evaporation. The residue was purified on a silica gel Mega Bond Elut column, eluting with 5-40% ethyl acetate/hexane to give the title compound (0.085 g) as a glass. MS: 419 (M−H)−.

Workup

  1. temperatureto cool to room temperature
  2. additionpoured onto a Varian Chem Elut column
  3. washwas eluted with ethyl acetate
  4. concentrationthe eluate was concentrated by evaporation
  5. customThe residue was purified on a silica gel Mega Bond Elut column
  6. washeluting with 5-40% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a641ed30f9654c4fb575256e65fcb0f9
Source dataset
uspto-grants-2002_04
Patent number
US06369273B1

Reaction notes

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