Triphenylphosphine → HCID 67527125, compound

HRID 15178Notes

Reaction equation

HRID 15178 reaction equation
O[CH2:2][CH2:3][C:4]1[C:5](=[O:11])[NH:6][NH:7][C:8](=[O:10])[CH:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OC(C)C)=O)=N\C(OC(C)C)=O>C1COCC1>[N:6]1[NH:7][C:8](=[O:10])[CH:9]=[C:4]2[CH2:3][CH2:2][O:11][C:5]=12

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67526953HCID 67526953, compound

Product 1

HCID 67527125HCID 67527125, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 4-(2-hydroxyethyl)-1,2-dihydro-3,6-pyridazinedione (2.7 g) in THF (200 ml) was treated with triphenylphosphine (6.6 g) and bis(1-methylethyl) (E)-1,2-diazenedicarboxylate (5.0 ml) was warmed to 40° C. After 3 hours the mixture was evaporated and chromatographed onto silica which was added to the top of a column. Chromatography eluting with 0-10% methanol in DCM afforded impure product (420 mg) which was further purified by chromatography in a similar manner affording the product (390 mg).

Workup

  1. customAfter 3 hours the mixture was evaporated
  2. customchromatographed onto silica which
  3. additionwas added to the top of a column
  4. washChromatography eluting with 0-10% methanol in DCM afforded impure product (420 mg) which
  5. customwas further purified by chromatography in a similar manner

Sources & evidence

ORD record
ord-6a3e3574b95f43f89e44de31b6b1c886
Source dataset
uspto-grants-2010_06
Patent number
US07732460B2

Reaction notes

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