Triethylamine → HCID 10682765, compound

HRID 974195Notes

Reaction equation

HRID 974195 reaction equation
C[C@H:2]([C:15](O)=O)[C:3]1[CH:4]=[CH:5][C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[CH:10][C:11]=2[CH:12]=1.C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C[Si]([NH:46][OH:47])(C)C.[NH4+].[Cl-]>C1C=CC=CC=1>[OH:47][NH:46][C:23](=[O:32])[NH:20][CH:2]([C:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:13][CH3:14])[CH:7]=2)[CH:12]=1)[CH3:15]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 156391NaproxenHCID 199401P,P-Diphenylphosphinic azideHCID 21936899N-Hydroxy-1,1,1-trimethylsilanamine

Product 1

HCID 10682765HCID 10682765, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of naproxen (2.0 g, 8.7 mmol) in benzene (45 mL) was added triethylamine (0.88 g, 8.7 mmol) followed by diphenylphosphoryl azide (2.39 g, 8.7 mmol) and the mixture was heated at 90° C. for one hour. Then, O- trimethylsilylhydroxylamine (1.83 g, 17.4 mmol) was added and the mixture was heated at 90° C. for 4 hours. The reaction was then poured into aqueous saturated NH4Cl (30 mL) and extracted with ethylacetate (3×50 mL). The combined organic extract was dried over MgSO4 and concentrated. The resulting residue was purified by crystallization from ethylacetate-hexane to provide the desired product (911 mg).

Workup

  1. temperaturethe mixture was heated at 90° C. for 4 hours
  2. extractionextracted with ethylacetate (3×50 mL)
  3. extractionThe combined organic extract
  4. dry with materialwas dried over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by crystallization from ethylacetate-hexane

Sources & evidence

ORD record
ord-9d1c1173192c4b508c6029ee1e7578a0
Source dataset
uspto-grants-1991_11
Patent number
US05068251

Reaction notes

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