Benzene → HCID 13576942, compound

HRID 544711Notes

Reaction equation

HRID 544711 reaction equation
[C:1]([O-:9])(=[O:8])[C:2]1C=CC=C[CH:3]=1.[NH2+:10]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.O.[CH:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[N:10]1([C:18]2[CH:23]=[CH:22][C:21]3[CH:2]([CH3:3])[C:1](=[O:8])[O:9][C:20]=3[CH:19]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 3

HCID 241BenzeneHCID 962WaterHCID 70504428HCID 70504428, compound

Product 1

HCID 13576942HCID 13576942, compound

Procedure

A mixture of 18.2 g (0.1 mole) of 4-methyl-3-(3-oxobutyl)-maleic acid anhydride and 23.2 g (0.105 mole) of hexahydroazepinium benzoate in 400 ml of benzene is heated under reflux for 48 hours using a water separator. The benzene is removed in vacuo and the residue remaining is partitioned between methylene chloride and saturated sodium bicarbonate solution. The crude product remaining after drying and after removal of the methylene chloride is chromatographed over silica gel with petroleum ether/ether. Subsequent recrystallisation from ether/petroleum ether yields 6-(hexahydroazepin-1-yl)-3-methylbenzofuran-2(3H)-one having a melting point of 57°-59° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 48 hours
  3. customThe benzene is removed in vacuo
  4. customthe residue remaining is partitioned between methylene chloride and saturated sodium bicarbonate solution
  5. customafter drying
  6. customafter removal of the methylene chloride
  7. customis chromatographed over silica gel with petroleum ether/ether
  8. customSubsequent recrystallisation from ether/petroleum ether

Sources & evidence

ORD record
ord-98ab112adb914d179cc385c0e2e9f91b
Source dataset
uspto-grants-1984_05
Patent number
US04451462

Reaction notes

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