Pyrrolidine → 6-Nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole

HRID 219647Notes

Reaction equation

HRID 219647 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].N1CC[CH2:24][CH2:23]1>CN(C=O)C>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH:1]=[CH:19][N:17]3[CH2:16][CH2:24][CH2:23][CH2:18]3)[O:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 797662-Methyl-6-nitrobenzoxazole

Product 1

HCID 866232146-Nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-methyl-6-nitro-benzoxazole (30 mmol), dimethyl formamide dimethyl acetal (60 mmol) and pyrrolidine (60 mmol) in DMF (45 mL) is stirred at 100° C. for 16 hours. The reaction mixture is concentrated in vacuo. The residue is dissolved in EtOAc, washed with water and brine, dried (Na2SO4) and filtered. The filtrate is concentrated. The residue is washed with cooled EtOAc to afford 6-nitro-2-(2-pyrrolidin-1-yl-vinyl)-benzooxazole as a solid. 1H NMR (300 MHz, CDCl3): δ 1.80-2.25 (broad, 4H), 3.10-3.80 (broad, 4H), 5.06 (d, H), 7.44 (d, H), 7.96 (d, H), 8.21 (m, 2H).

Workup

  1. concentrationThe reaction mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. washThe residue is washed with cooled EtOAc

Sources & evidence

ORD record
ord-08e8bfd92a364983b2bc4be78aaccad9
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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