Water → HCID 86615503, compound

HRID 2358768Notes

Reaction equation

HRID 2358768 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([CH:13](O)[CH3:14])=[CH:9][CH:8]=2)=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.C1(P([N:35]=[N+:36]=[N-:37])(C2C=CC=CC=2)=O)C=CC=CC=1.O>C1(C)C=CC=CC=1>[N:35]([CH:13]([C:10]1[CH:11]=[CH:12][C:7]([O:6][C:5]2[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][C:4]=2[N+:18]([O-:20])=[O:19])=[CH:8][CH:9]=1)[CH3:14])=[N+:36]=[N-:37]

Participants

5

Reactant 3

HCID 962WaterHCID 199401P,P-Diphenylphosphinic azideHCID 43506274HCID 43506274, compound

Product 1

HCID 86615503HCID 86615503, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

To the product from Example 164b (0.30 g, 1.0 mmol) in toluene (20 mL) was added diphenylphosphoryl azide (0.36 g 6.26 mmol), followed by 1,8-diazabicyclo[4.3.0]undec-7-ene (0.19 g, 1.3 mmol). The mixture is stirred at 25° C. for 18 h. The reaction was poured into water and extracted with ethyl acetate. The combined organic layers are washed with 5% HCl, sat. NaCl (1×), dried over sodium sulfate, filtered and concentrated under vacuum giving the crude title compound. The crude product was purified by silica gel chromatography, eluting with hexanes/ethyl acetate/methanol (85:15:5) to provide the title compound (300 mg, 94%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers are washed with 5% HCl, sat. NaCl (1×)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customgiving the crude title compound
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with hexanes/ethyl acetate/methanol (85:15:5)

Sources & evidence

ORD record
ord-3c195796847c4c68a5bf3a96e788f093
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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