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Triphenylphosphine → HCID 66863232, compound

HRID 253057
Notes
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Reaction equation

HRID 253057 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[C:11]([OH:20])[C:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[N:9]1.[C:26]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:27]=1.[O:45]1[CH2:50][CH2:49][N:48]([CH2:51][CH2:52]O)[CH2:47][CH2:46]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH2:26]([N:9]1[CH:10]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:11]([O:20][CH2:52][CH2:51][N:48]2[CH2:49][CH2:50][O:45][CH2:46][CH2:47]2)=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[N:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:27]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 611632-MorpholinoethanolHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 24828929HCID 24828929, compound

Product 1

HCID 66863232HCID 66863232, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of 1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-ethoxycarbonyl-4-hydroxy-1H-pyrazole (200 mg, compound obtained in Reference Example 1 (4)) in tetrahydrofuran (4 mL) was added triphenylphosphine (208 mg) and 2-morpholino-ethanol (96 μL) and the mixture was stirred. Thereto was added dropwise diisopropyl azodicarboxylate (154 μL) at 0° C. under nitrogen-gas atmosphere and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and the crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=67/33 to 30/70) to obtain ethyl 1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-ethoxycarbonyl-4-(2-morpholinoethoxy)-1H-pyrazole (463 mg, yield: 100%) as a colorless viscidity.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe crude product was purified by column chromatography on silica gel (solvent: hexane/ethyl acetate=67/33 to 30/70)

Sources & evidence

ORD record
ord-28bd15e72d1244309d6a7d84390d328b
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07872006B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes