Acetamide → HCID 21495355, compound

HRID 1731143Notes

Reaction equation

HRID 1731143 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][OH:12])=[CH:2]1.[C:13]([NH2:16])(=[O:15])[CH3:14]>C1C=CC=CC=1>[C:13]([NH:16][CH2:3][CH2:2][CH2:1][C:9]1([CH3:8])[C:2]2[CH2:1][C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:3]=2[CH2:10][CH2:11][O:12]1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 178AcetamideHCID 113556481H-Indene-3-ethanol

Product 1

HCID 21495355HCID 21495355, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of indene-3-ethanol (4.2 g) and N-(4-oxopentyl(acetamide (3.7 g), described by L. P. Kuhn et al., J. Am. Chem. Soc., 89, 3858 (1967), in 300 ml of dry benzene is stirred and heated at reflux. Water is collected in a Dean-Stark trap. After removal of the water five drops of boron trifluoride-etherate is added and the mixture refluxed 30 min. using the water-separator again. After stirring at room temperature overnight the reaction mixture is evaporated to dryness. The solid residue is dissolved in chloroform and washed successively with 10% aqueous sodium bicarbonate, water, and brine. The chloroform solution is dried over magnesium sulfate, filtered, and evaporated to yield 1-[3-(acetamido)propyl]-1-methyl-1,3,4,9-tetrahydroindeno[2,1-c]pyran, νmaxCHCl3 1650 cm-1.

Workup

  1. temperatureheated
  2. temperatureat reflux
  3. customWater is collected in a Dean-Stark trap
  4. customAfter removal of the water five drops of boron trifluoride-etherate
  5. additionis added
  6. temperaturethe mixture refluxed 30 min.
  7. customis evaporated to dryness
  8. dissolutionThe solid residue is dissolved in chloroform
  9. washwashed successively with 10% aqueous sodium bicarbonate, water, and brine
  10. dry with materialThe chloroform solution is dried over magnesium sulfate
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-81faf44b84f9443c9407a3f4327a6164
Source dataset
uspto-grants-1976_11
Patent number
US03995052

Reaction notes

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