Water → HCID 356672, compound

HRID 1639020Notes

Reaction equation

HRID 1639020 reaction equation
[H-].[Na+].[CH3:3][NH:4][C:5](=[O:7])[CH3:6].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]Br.[OH2:16]>C1COCC1>[CH3:3][N:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][N:4]([CH3:3])[C:5](=[O:16])[CH3:6])[C:5](=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 6582N-MethylacetamideHCID 123681,6-DibromohexaneHCID 24758Sodium hydride

Product 1

HCID 356672HCID 356672, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a 50% oil suspension of sodium hydride (3.36 grams, 70 mmol) in dry THF (60 mL) under nitrogen was added N-methylacetamide (5.0 grams, 69 mmol) in 10 mL THF, and the mixture was refluxed for five hours. Then, 6.0 grams (24 mmol) of 1,6-dibromohexane was added, and the resulting mixture was refluxed for an additional two hours. Two hundred milliliters of cold water was added, and the aqueous phase was extracted with 100 mL of chloroform three times. The organic layer was washed with water and dried over magnesium sulfate, and the solvent was evaporated in vacuo to yield an oil. Kugelrohr distillation of this material gave 2.5 grams of a pure oil (53%), boiling point 138° C. (0.1 torr).

Workup

  1. temperaturethe mixture was refluxed for five hours
  2. temperaturethe resulting mixture was refluxed for an additional two hours
  3. extractionthe aqueous phase was extracted with 100 mL of chloroform three times
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customto yield an oil
  8. distillationKugelrohr distillation of this material

Sources & evidence

ORD record
ord-9156dcc615f04bf2b24de99dc36dbcc3
Source dataset
uspto-grants-1989_11
Patent number
US04882346

Reaction notes

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