Ethanol → HCID 21507054, compound

HRID 1287936Notes

Reaction equation

HRID 1287936 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:19]=[CH:18][C:17]2=[C:20]3[C:6]=1[CH:7]=[CH:8][CH:9]=[C:10]3[C:11](=[O:25])[C:12]1[C:13]3[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=3[O:15][C:16]=12.[CH2:26]([NH2:28])[CH3:27].[CH2:29](O)[CH3:30]>>[CH2:26]([N:28]([CH2:29][CH3:30])[CH2:2][CH2:3][O:4][C:5]1[CH:19]=[CH:18][C:17]2=[C:20]3[C:6]=1[CH:7]=[CH:8][CH:9]=[C:10]3[C:11](=[O:25])[C:12]1[C:13]3[CH:24]=[CH:23][CH:22]=[CH:21][C:14]=3[O:15][C:16]=12)[CH3:27]

Participants

4

Reactant 3

HCID 702EthanolHCID 6341EthylamineHCID 21507051HCID 21507051, compound

Product 1

HCID 21507054HCID 21507054, compound

Procedure

A suspension of 4.4. g. (11.2 mmol.) of 3-(2-bromoethoxy)-7-oxo-7H-benzo[b]phenaleno[2,1-d]furan and 10 ml. of ethylamine in 250 ml. of absolute ethanol was refluxed for 4 days. The reaction mixture was filtered while hot, the filtrate was evaporated to dryness and the semi-solid residue was dissolved in methylene chloride. The methylene chloride solution was extracted twice with dilute sodium hydroxide solution and once with water, dried (MgSO4) and evaporated to dryness to give a residue which was crystallized from hexane to give the title compound, m.p. 115°-118°.

Workup

  1. additionA suspension of 4.4
  2. filtrationThe reaction mixture was filtered while hot, the filtrate
  3. customwas evaporated to dryness
  4. dissolutionthe semi-solid residue was dissolved in methylene chloride
  5. extractionThe methylene chloride solution was extracted twice with dilute sodium hydroxide solution and once with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customto give a residue which
  9. customwas crystallized from hexane

Sources & evidence

ORD record
ord-5ee6177586b34c58a3291cf6b301e2a8
Source dataset
uspto-grants-1976_10
Patent number
US03985896

Reaction notes

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