Water → HCID 21860915, compound

HRID 2359936Notes

Reaction equation

HRID 2359936 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([S:7]([CH2:10][N+:11]#[C-:12])(=[O:9])=[O:8])=[CH:3][CH:2]=1.CN(C)C(N(C)C)=N.C(O[CH:26]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:27]([N+]([O-])=O)[CH3:28])(=O)C.O>O1CCCC1.C(O)(C)C>[CH3:28][C:27]1[C:26]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:10]([S:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=2)(=[O:8])=[O:9])[NH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 664601,1,3,3-TetramethylguanidineHCID 161915Tosylmethyl isocyanideHCID 124048832-nitro-1-phenylpropyl Acetate

Product 1

HCID 21860915HCID 21860915, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of p-toluenesulfonylmethyl isocyanide (6.1 g) and 1,1,3,3-tetramethylguanidine (8.3 mL) in tetrahydrofuran (18 mL) and isopropyl alcohol (18 mL) was added dropwise a solution of 2-nitro-1-phenylpropyl acetate (7.0 g) in tetrahydrofuran (3 mL) and isopropyl alcohol (3 mL), and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound as a white solid (yield 6.1 g, 63%).

Workup

  1. extractionthe mixture was extracted with a mixed solvent of ethyl acetate and tetrahydrofuran
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c90a1e57d2124e3b8906ff80dc4e4ddf
Source dataset
uspto-grants-2014_04
Patent number
US08686010B2

Reaction notes

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