Dimethyl Sulfoxide → HCID 54373809, compound

HRID 2298070Notes

Reaction equation

HRID 2298070 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 h. The mixture was then cooled, diluted with ethyl acetate (200 ml), washed with 2N aqueous hydrochloric acid (200 ml), dried (MgSO4) then concentrated. Purification of the residue by silica gel chromatography (eluting with 20% ethyl acetate in isohexane) gave the subtitle compound (1.744 g).

Workup

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

Sources & evidence

ORD record
ord-db56f1d83b904c1a88e67d32204ce7f6
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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