Iodine → HCID 54443354, compound

HRID 1283297Notes

Reaction equation

HRID 1283297 reaction equation
II.[CH:3]12[C:15](=[O:16])[CH:7]3[C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[CH:10]1[CH:4]2[C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=13.[CH3:21][N:22]([CH3:27])[C:23](=[O:26])[CH2:24]Br>[Zn].C1C=CC=CC=1.CO.C(O)(=O)C>[CH3:21][N:22]([CH3:27])[C:23](=[O:26])[CH2:24][C:15]1([OH:16])[CH:7]2[C:8]3[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=3[CH:10]3[CH:3]1[CH:4]3[C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=12

Participants

8

Reactant 3

HCID 807IodineHCID 2255442-Bromo-N,N-dimethylacetamideHCID 12117541HCID 12117541, compound

Product 1

HCID 54443354HCID 54443354, compound

Reagents, catalysts & solvents 4

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 241BenzeneSolvent3×HCID 887MethanolSolvent

Procedure

An amount of 3.6 g (0.055 mole) of zinc chips and a trace of iodine are placed into a dry reaction vessel; additions are then made of 2 ml of a solution of 7.0 g (0.03 mole) of 1,1a,6,10b-tetrahydro-1,6-methano-dibenzo[a,e]cyclopropa[c]cyclohepten-11-one and 7.1 g (0.039 mole) of N,N-dimethyl-bromoacetamide in 50 ml of abs. benzene, and the whole is refluxed while stirring is maintained; the remainder of the benzene solution is added dropwise in the course of 30 minutes and refluxing subsequently performed for a further hour. After cooling, the reaction mixture is decomposed with 6 ml of glacial acetic acid and 6 ml of methanol. The formed organic precipitate is taken into solution by the addition of benzene and zinc residues still present are filtered off. The benzene solution is washed with 2N acetic acid, then with 2N sodium bicarbonate solution and finally with water; it is then dried over sodium sulphate and concentrated in a water-jet vacuum. The residue crystallises from benzene/petroleum ether to yield N,N-dimethyl-11-hydroxy-1,1a,6,10b-tetrahydro-1,6-methano-dibenzo[a,e] cyclopropa[c]cycloheptene-11-acetamide; M.P. 203°-204°.

Workup

  1. temperatureis maintained
  2. temperaturerefluxing subsequently
  3. waitperformed for a further hour
  4. temperatureAfter cooling
  5. filtrationstill present are filtered off
  6. washThe benzene solution is washed with 2N acetic acid
  7. dry with materialit is then dried over sodium sulphate
  8. concentrationconcentrated in a water-jet vacuum
  9. customThe residue crystallises from benzene/petroleum ether

Sources & evidence

ORD record
ord-88b8a930f4ad4a53a249fc28fb627bf7
Source dataset
uspto-grants-1976_08
Patent number
US03974284

Reaction notes

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