Triphenylphosphine → Ethyl {3-[3-(4-hydroxyphenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}carbamate

HRID 2093348Notes

Reaction equation

HRID 2093348 reaction equation
[O:1]=[C:2]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11](C(OC(C)(C)C)=O)=[CH:10][CH:9]=2)[CH:4]=[CH:3]1.O[CH2:22][C:23]1[CH:24]=[C:25]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])[CH:26]=[CH:27][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=[O:57]>C1COCC1>[OH:57][C:11]1[CH:10]=[CH:9][C:8]([C:5]2[CH:4]=[CH:3][C:2](=[O:1])[N:7]([CH2:22][C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:34])[O:31][CH2:32][CH3:33])[CH:26]=[CH:27][CH:28]=3)[N:6]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10607893Ethyl (3-hydroxymethylphenyl)carbamateHCID 68516886Tert-butyl 4-(6-oxo-1,6-dihydropyridazin-3-yl)phenyl-carboxylate

Product 1

HCID 136168092Ethyl {3-[3-(4-hydroxyphenyl)-6-oxo-6H-pyridazin-1-ylmethyl]phenyl}carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5 g (17.3 mmol) of tert-butyl 4-(6-oxo-1,6-dihydropyridazin-3-yl)phenylcarboxylate, 5.08 g (26 mmol) of ethyl (3-hydroxymethylphenyl)carbamate and 6.8 g (26 mmol) of triphenylphosphine are dissolved in 400 ml of THF. Under a nitrogen atmosphere, the yellow solution is cooled to 0° C., 4.1 ml (26 mmol) of diethyl azodicarboxylate are slowly added dropwise, and the reaction mixture is stirred at room temperature for 20 h. The yellow suspension is evaporated to dryness. The residue is dissolved in 300 ml of dichloromethane, and 40 ml of trifluoroacetic acid are added. The reaction mixture is stirred at room temperature for 20 h, evaporated to dryness, and 100 ml of water, 200 ml of 1N NaOH and 100 ml of ethyl acetate are added to the viscous oil. A precipitate forms in the process, which is filtered off with suction, washed with water and dried in vacuo.

Workup

  1. customThe yellow suspension is evaporated to dryness
  2. dissolutionThe residue is dissolved in 300 ml of dichloromethane
  3. addition40 ml of trifluoroacetic acid are added
  4. stirringThe reaction mixture is stirred at room temperature for 20 h
  5. customevaporated to dryness, and 100 ml of water, 200 ml of 1N NaOH and 100 ml of ethyl acetate
  6. additionare added to the viscous oil
  7. filtrationA precipitate forms in the process, which is filtered off with suction
  8. washwashed with water
  9. customdried in vacuo

Sources & evidence

ORD record
ord-71a13cad771748e5879a041cf80ad760
Source dataset
uspto-grants-2013_05
Patent number
US08445489B2

Reaction notes

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