Hexachloroethane → HCID 71087339, compound

HRID 927367Notes

Reaction equation

HRID 927367 reaction equation
[CH:1]([NH:3][NH:4][C:5](=[O:20])[C:6]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([CH3:8])[CH3:7])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(C(C)C)C(C)C.ClC(Cl)(Cl)C(Cl)(Cl)Cl>C(#N)C>[O:20]1[CH:1]=[N:3][N:4]=[C:5]1[C:6]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)([CH3:7])[CH3:8]

Participants

6

Reactant 4

HCID 6214HexachloroethaneHCID 11776TriphenylphosphineHCID 81531DiisopropylethylamineHCID 71087476HCID 71087476, compound

Product 1

HCID 71087339HCID 71087339, compoundYield 127.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of benzyl 1-(2-formylhydrazinyl)-2-methyl-1-oxopropan-2-ylcarbamate (0.9 g, 3 mmol) and PPh3 (CAN 603-35-0, 1.268 g, 5 mmol) in acetonitrile (20 mL) was added DIPEA (CAN 7087-68-5, 1.249 g, 10 mmol) and hexachloroethane (CAN 67-72-1, 0.991 g, 4 mmol). The reaction mixture was stirred at room temperature under nitrogen atmosphere for 4 h. After evaporation of solvents, the residue was diluted with ethyl acetate (30 mL) and water (30 mL). The organic layer was washed with brine (30 mL), dried over anhydrous sodium sulfate and evaporated. The remaining residue was then purified by column chromatography (silica gel, 30 g, eluting with 10% ethyl acetate in petroleum ether) to give the title compound (1 g, 30% purity, 36%) as colorless oil containing OPPh3 and PPh3; MS: m/e 262.2 [M+H]+.

Workup

  1. customAfter evaporation of solvents
  2. additionthe residue was diluted with ethyl acetate (30 mL) and water (30 mL)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe remaining residue was then purified by column chromatography (silica gel, 30 g, eluting with 10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-9741f598c62443dd837640b97eb59bbf
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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