Dimethyl Sulfoxide → HCID 66712571, compound

HRID 1262318Notes

Reaction equation

HRID 1262318 reaction equation
COC([CH:5]1[CH2:10][C:9]([C:22]#[N:23])([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[C:13]([O:20][CH3:21])[CH:12]=2)[CH2:8][CH2:7][C:6]1=[O:24])=O.[Cl-].[Na+].O.CS(C)=O>>[CH3:21][O:20][C:13]1[CH:12]=[C:11]([C:9]2([C:22]#[N:23])[CH2:8][CH2:7][C:6](=[O:24])[CH2:5][CH2:10]2)[CH:16]=[CH:15][C:14]=1[N+:17]([O-:19])=[O:18]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 5234Sodium ChlorideHCID 66712110HCID 66712110, compound

Product 1

HCID 66712571HCID 66712571, compound

Conditions

Temperature
165 °C

Procedure

Into a 8-dram vial, 5-Cyano-5-(3-methoxy-4-nitro-phenyl)-2-oxo-cyclohexanecarboxylic acid methyl ester (2.00 g, 6.02 mmol), Sodium chloride (1.00 g, 17.1 mmol), Water (1.00 mL, 55.5 mmol) and Dimethyl sulfoxide (5.00 g, 64.0 mmol) were added. The reaction mixture was heated at 165° C. for 6 hours. HPLC suggested no SM. The reaction was partitioned with water and EtOAc. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol). The collected fractions afforded 1-(3-Methoxy-4-nitro-phenyl)-4-oxo-cyclohexanecarbonitrile a white solid (0.80 g, 48%).

Workup

  1. customThe reaction was partitioned with water and EtOAc
  2. customThe organic was separated
  3. washwashed with Brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe solid was filtered
  6. washwashed with DCM
  7. customThe solvent was removed under vacuum
  8. customThe reaction mixture was purified via ISCO column chromatography with DCM and methanol as eluant (0 to 10% methanol)

Sources & evidence

ORD record
ord-86b0edda2800494cbf8885fc7b64995d
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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