Triphenylphosphine → HCID 19824167, compound

HRID 728335Notes

Reaction equation

HRID 728335 reaction equation
O[CH2:2][CH2:3][NH:4][C:5]([CH2:7][C:8]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=1[Cl:23])([OH:15])[CH2:9][N:10]1[CH:14]=[N:13][CH:12]=[N:11]1)=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O>[N:4]1([C:5]([CH2:7][C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])([OH:15])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[O:6])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19824168HCID 19824168, compound

Product 1

HCID 19824167HCID 19824167, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1(N-[2-Hydroxyethyl]carbamoyl)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol (1.0 g), triphenylphosphine (1.09 g) and diethyl azodicarboxylate (0.72 g) were stirred at room temperature for 20 hours in dry tetrahydrofuran (20 ml). The reaction mixture was then diluted with water (70 ml) and extracted with ethyl acetate (3×5 ml). The combined organic extracts were washed with saturated sodium chloride solution (2×20 ml), dried (MgSO4), and evaporated to a brown gum. This material was chromatographed on Merck "Kieselgel 60" silica, eluting with 5% by volume ethanol in ether increasing to 10% ethanol in ether. The eluted material, which was one compound as judged by thin-layer chromatography, was crystallized from ethyl acetate/n-pentane to give colorless crystals of the title compound, 441 mg, m.p. 151°-153° C.

Workup

  1. extractionextracted with ethyl acetate (3×5 ml)
  2. washThe combined organic extracts were washed with saturated sodium chloride solution (2×20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a brown gum
  5. customThis material was chromatographed on Merck "Kieselgel 60" silica
  6. washeluting with 5% by volume ethanol in ether increasing to 10% ethanol in ether
  7. customwas crystallized from ethyl acetate/n-pentane

Sources & evidence

ORD record
ord-6e038727f4684546a5d5e268622db136
Source dataset
uspto-grants-1991_09
Patent number
US05047548

Reaction notes

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