Water → HCID 68871013, compound

HRID 1986349Notes

Reaction equation

HRID 1986349 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[H-].[Na+].Cl[C:15]1[CH:20]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][Si](C(C)(C)C)(C)C)=[CH:24][CH:23]=2)[C:18]([N+:36]([O-:38])=[O:37])=[CH:17][N:16]=1.O>CN(C=O)C>[OH:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][C:19]2[C:18]([N+:36]([O-:38])=[O:37])=[CH:17][N:16]=[C:15]([O:11][C:7]3[CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=[CH:9][CH:8]=3)[CH:20]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 121243-HydroxyacetanilideHCID 24758Sodium hydrideHCID 86623344HCID 86623344, compound

Product 1

HCID 68871013HCID 68871013, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of 3-acetamidophenol (10.8 g, 72 mmol) in DMF (50 mL) was added dropwise to a slurry of NaH (60% in oil, 2.88 g, 72 mmol) over 1 h. A solution of the product from Step 1 (13.7 g, 36.0 mmol) in DMF (50 mL) was added and the resulting mixture was heated to 60° C. overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic layers were combined, washed with brine, dried (MgSO4), filtered and the filtrate was concentrated to give an oil which was purified by chromatography (10-100% EtOAc in hexanes) to give the title compound (4.6 g, 34%) as an orange solid. MS (ES+) m/e 381 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customto give an oil which
  7. customwas purified by chromatography (10-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a2167b6220d5418cbe0ac21ba03412f4
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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