Dimethyl Sulfoxide → HCID 54373809, compound

HRID 1267926Notes

Reaction equation

HRID 1267926 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=1.[C:12]([O:16][C:17](=[O:24])[NH:18][CH:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+].CS(C)=O>C(OCC)(=O)C>[C:12]([O:16][C:17](=[O:24])[NH:18][CH:19]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH3:11])[CH:3]=2)[CH2:20]1)([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 949565-Fluoro-2-nitrotolueneHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 54373809HCID 54373809, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Fluoro-2-methyl-1-nitrobenzene (1 g), pyrrolidin-3-ylcarbamic acid tert-butyl ester (1.2 g), potassium carbonate (1.79 g) and dimethyl sulfoxide (10 ml) were heated together at 80° C. under nitrogen for 15 hours. The mixture was cooled, diluted with ethyl acetate (200 ml), washed with 2M aqueous hydrochloric acid (200 ml), dried (MgSO4), and concentrated. Purification of the residue by silica gel chromatography (eluting with 20% ethyl acetate in isohexane) gave the sub-title compound (1.744 g) as a yellow solid.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with 2M aqueous hydrochloric acid (200 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customPurification of the residue
  6. washby silica gel chromatography (eluting with 20% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-800d2631ce5c44a4807cacb694ea6f46
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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