Sodium Carbonate → 2'-Amino-2-methoxy-1'-methyl-7-bromo-10,11-dihydrospiro[dibenzo[a,d][7]-annulene-5,4'-imidazol]-5'(1'H)-one

HRID 730180Notes

Reaction equation

HRID 730180 reaction equation
[Br:1][C:2]1[CH:22]=[CH:21][C:5]2[CH2:6][CH2:7][C:8]3[C:17](C)=[C:16]([O:19][CH3:20])[CH:15]=[CH:14][C:9]=3[C:10](=[O:13])[C:11](=O)[C:4]=2[CH:3]=1.[CH3:23][NH:24][C:25]([NH2:27])=[NH:26].C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(O)C.O>[NH2:27][C:25]1[N:24]([CH3:23])[C:10](=[O:13])[C:11]2([C:9]3[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][C:8]=3[CH2:7][CH2:6][C:5]3[CH:21]=[CH:22][C:2]([Br:1])=[CH:3][C:4]2=3)[N:26]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 578344828-Bromo-2-methoxy-1-methyl-11,12-dihydro-dibenzo[a,e]cyclooctene-5,6-dioneHCID 178485088HCID 178485088, compound

Product 1

HCID 249832682'-Amino-2-methoxy-1'-methyl-7-bromo-10,11-dihydrospiro[dibenzo[a,d][7]-annulene-5,4'-imidazol]-5'(1'H)-oneYield 57%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of 8-bromo-2-methoxy-1-methyl-11,12-dihydro-dibenzo[a,e]cyclo-octene-5,6-dione 13 (2.49 g; 6.9 mmol) in dioxane and ethanol was treated with N-methylguanidine (1.52 g, 13.9 mmol), followed by a solution of sodium carbonate (1.47 g; 13.9 mmol) in water, heated at 85° C. for 3 hours, cooled and concentrated in vacuo. The resultant residue was taken up in chloroform and washed with water. The chloroform phase was separated, dried over magnesium sulfate and evaporated. This residue was crystallized from ethyl acetate and hexane to give the title product as a tan powder, 1.62 g (57% yield, identified by NMR and mass spectral analyses.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. washwashed with water
  4. customThe chloroform phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThis residue was crystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-1cf9479ec53c451ba85d442108bb9e14
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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