Dimethyl Sulfoxide → HCID 70145969, compound

HRID 574274Notes

Reaction equation

HRID 574274 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[NH2:13][CH:14]1[CH2:17][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]1.C(N(CC)CC)C.CS(C)=O>O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([NH:13][CH:14]2[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 70145969HCID 70145969, compoundYield 116.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

Into a 100 mL 3-Neck round-bottomed flask equipped with reflux condenser were charged 4-fluoro-2-methoxy-1-nitrobenzene (4.086 g) and tert-butyl 3-aminoazetidine-1-carboxylate (4.4 g), triethylamine (9.6 mL), and dimethyl sulfoxide (20 mL). The reaction mixture was heated at 95° C. for 8 hours. The reaction mixture was poured into water (200 mL) and extracted with ethyl acetate (50 mL×3). The organic layer was washed with brine (50 mL×2), dried over sodium sulfate, and concentrated completely under reduced pressure at 40° C. to give the title compound (9 g) which was used without further purification.

Workup

  1. customInto a 100 mL 3-Neck round-bottomed flask equipped
  2. temperaturewith reflux condenser
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. washThe organic layer was washed with brine (50 mL×2)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated completely under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-75cb68a1e1ff47eaa46864cb7f58887f
Source dataset
uspto-grants-2015_05
Patent number
US09034885B2

Reaction notes

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