Dimethylformamide → HCID 68872196, compound

HRID 1986360Notes

Reaction equation

HRID 1986360 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+].[C:14]([O:18][C:19]([N:21]1[CH2:30][CH2:29][C:28]2[C:23](=[CH:24][C:25]([NH:31][C:32]3[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][N:35]=[C:34](Cl)[CH:33]=3)=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].CN(C=O)C>C1COCC1>[C:14]([O:18][C:19]([N:21]1[CH2:30][CH2:29][C:28]2[C:23](=[CH:24][C:25]([NH:31][C:32]3[C:37]([N+:38]([O-:40])=[O:39])=[CH:36][N:35]=[C:34]([O:11][C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:6]=4)[CH:33]=3)=[CH:26][CH:27]=2)[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 121243-HydroxyacetanilideHCID 24758Sodium hydrideHCID 86623346HCID 86623346, compound

Product 1

HCID 68872196HCID 68872196, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-acetamidophenol (4.8 g, 32 mmol) in THF (200 mL) was cooled to 0° C. To the solution was added NaH (60% in oil, 1.3 g, 32 mol) and the mixture was warmed to rt and allowed to stir for 30 minutes. The product from Step 1 (˜8.5 g, ˜21 mmol) was added and the mixture was stirred at rt overnight then DMF (10 mL) was added and the solution was heated to 60° C. overnight. The reaction mixture was concentrated in-vacuo, then taken up in EtOAc and H2O and extracted with EtOAc. The organic layers were combined, dried over MgSO4, filtered, and concentrated. The crude oil was purified chromatography to give the title compound (4.3 g, 39%). MS (ES+) m/e 521 [M+H]+.

Workup

  1. stirringthe mixture was stirred at rt overnight
  2. temperaturethe solution was heated to 60° C. overnight
  3. concentrationThe reaction mixture was concentrated in-vacuo
  4. extractionH2O and extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude oil was purified chromatography

Sources & evidence

ORD record
ord-860df9681d624299b39554155f8f11ea
Source dataset
uspto-grants-2009_06
Patent number
US07547779B2

Reaction notes

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