Ethyl Acetate → HCID 53922974, compound

HRID 1595869Notes

Reaction equation

HRID 1595869 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH:15]=[C:16]([Cl:18])[CH:17]=1)[O:7][CH2:8][CH2:9][NH:10][S:11]([CH3:14])(=[O:13])=[O:12].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].CCOC(C)=O>CN(C=O)C>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][N:10]([CH2:9][CH2:8][O:7][C:6]1[CH:15]=[C:16]([Cl:18])[CH:17]=[C:4]([Cl:3])[CH:5]=1)[S:11]([CH3:14])(=[O:12])=[O:13])[CH3:30]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 122490Ethyl 7-bromoheptanoateHCID 22246767HCID 22246767, compound

Product 1

HCID 53922974HCID 53922974, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of NaH (60% in oil, 338 mg, 8.45 mmol) in DMF (23 mL) was cooled to 0° C. followed by addition of N-[2-(3,5-dichloro-phenoxy)-ethyl]-methanesulfonamide (2.0 g, 7.04 mmol). The reaction was stirred at room temperature for 0.5 h and was cooled to 0° C. followed by addition of ethyl 7-bromoheptanoate (2.0 g, 8.45 mmol). The reaction was heated at 65° C. for 3 h and was cooled to room temperature. EtOAc was added and the organic solution was washed consecutively with 1 N HCl, water, and brine. The organic solution was dried (MgSO4), filtered, and concentrated. Purification by flash chromatography (4:1 hexanes:EtOAc) provided the title compound (2.84 9). 1HNMR (400 MHz, CDCl3) δ 6.95 (m, 1H), 6.75 (m, 2H), 4.06 (m, 5H), 3.56 (t, 2H), 3.22 (t, 2H), 2.86 (s, (t, 2H), 1.60 (m, 4H), 1.32 (m, 4H), 1.22 (t, 3H).

Workup

  1. temperaturewas cooled to 0° C.
  2. temperatureThe reaction was heated at 65° C. for 3 h
  3. temperaturewas cooled to room temperature
  4. washthe organic solution was washed consecutively with 1 N HCl, water, and brine
  5. dry with materialThe organic solution was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash chromatography (4:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-103d8b670a95494f93927c9bcfddf73e
Source dataset
uspto-grants-2001_09
Patent number
US06288120B1

Reaction notes

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