Triphenylphosphine → HCID 21875750, compound

HRID 724141Notes

Reaction equation

HRID 724141 reaction equation
[Cl:1][C:2]1[C:3]([C:23]([F:26])([F:25])[F:24])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH:19](O)[CH3:20])=[CH:14][CH:13]=3)[C:6]=2[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:60]=[N+:61]=[N-:62])(C2C=CC=CC=2)=O)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[N:60]([CH:19]([CH3:20])[CH2:18][C:15]1[CH:16]=[CH:17][C:12]([N:7]2[C:6]3[CH:22]=[C:2]([Cl:1])[C:3]([C:23]([F:26])([F:25])[F:24])=[CH:4][C:5]=3[N:9]=[C:8]2[CH2:10][CH3:11])=[CH:13][CH:14]=1)=[N+:61]=[N-:62]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21875633HCID 21875633, compound

Product 1

HCID 21875750HCID 21875750, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1-{4-[6-chloro-2-ethyl-5-(trifluoromethyl)-1H-benzimidazol-1-yl]phenyl}-2-propanol (step 8 of Example 247, 1.96 g, 5.12 mmol), triphenylphosphine (1.75 g, 6.66 mmol) and diphenylphosphoryl azide (1.83 mg, 6.66 mmol) in tetrahydrofuran (15 ml) was added diethyl azodicarboxylate (1.16 mg, 6.66 mmol) at room temperature. The resulting mixture was stirred at temperature for 3 h, then under reflux temperature. The mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried (Na2SO4), and concentrated. Purification by flash column chromatography eluting with hexane/ethyl acetate (2:1) and TLC developing with hexane/ethyl acetate (1:1) afforded 769 mg (37%) of the title compound as a slight yellow syrup.

Workup

  1. temperatureunder reflux temperature
  2. washwashed with water and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customPurification by flash column chromatography
  6. washeluting with hexane/ethyl acetate (2:1) and TLC

Sources & evidence

ORD record
ord-f0f23d46b4a74c9787349024fedef274
Source dataset
uspto-grants-2006_11
Patent number
US07141580B2

Reaction notes

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