N-bromobutanimide → HCID 23459804, compound

HRID 1732745Notes

Reaction equation

HRID 1732745 reaction equation
[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[CH2:14][CH:13]([C:18]([O:20][CH3:21])=[O:19])[O:12][C:11]=2[C:10]([CH2:22][CH2:23][CH3:24])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH2:8]2.BrN1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:16]2[C:15](=[O:17])[CH:14]=[C:13]([C:18]([O:20][CH3:21])=[O:19])[O:12][C:11]=2[C:10]([CH2:22][CH2:23][CH3:24])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][CH2:8]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20304590HCID 20304590, compound

Product 1

HCID 23459804HCID 23459804, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of methyl 2,3-dihydro-5-methoxy-4-oxo-10-propyl-6,7,8,9-tetrahydro-4H-naphtho[2,3-b]pyran-2-carboxylate (3.4 g) and N-bromosuccinimide (1.78 g) was heated at reflux in carbon tetrachloride (150 ml) for 6 hours. The solution was cooled, washed with water, dried (Na2SO4) and evaporated. The residue was crystallised from petroleum ether (60°-80°) giving the title compound as a fawn solid, mp 92°-3°.

Workup

  1. temperaturewas heated
  2. temperatureThe solution was cooled
  3. washwashed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was crystallised from petroleum ether (60°-80°)

Sources & evidence

ORD record
ord-e7e2d0ddb625436f86c1a298ccfe5395
Source dataset
uspto-grants-1980_12
Patent number
US04238606

Reaction notes

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