Acetonitrile → HCID 19000638, compound

HRID 2260394Notes

Reaction equation

HRID 2260394 reaction equation
C1(S[CH2:8][C:9]2[CH:22]=[C:21]3[C:12]([C:13](=[O:24])[C:14]4[C:19]([C:20]3=[O:23])=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:11]3[CH2:25][CH2:26][CH2:27][C:10]=23)C=CC=CC=1.N#C[Br:30].C(#N)C>>[Br:30][CH2:8][C:9]1[CH:22]=[C:21]2[C:12]([C:13](=[O:24])[C:14]3[C:19]([C:20]2=[O:23])=[CH:18][CH:17]=[CH:16][CH:15]=3)=[C:11]2[CH2:25][CH2:26][CH2:27][C:10]=12

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 10476Cyanogen BromideHCID 19000729HCID 19000729, compound

Product 1

HCID 19000638HCID 19000638, compoundYield 61%

Procedure

A mixture of 2,3-dihydro-4-phenylthiomethyl-1H-cyclopent[a]-anthracene-6,11-dione (350 mg, 0.95 mmol) and cyanogen bromide solution (5.0M) in acetonitrile (8 mL, 4 mmol) is heated at reflux for 4.5 hours under nitrogen. After cooling, the mixture is washed with H2O (20 mL×3), dried (Na2SO4) and evaporated in vacuo to dryness. The residue is then treated with boiling ethyl ether for 10 minutes and then stored in the refrigerator overnight. The product, 2,3-dihydro-4-bromomethyl-1H-cyclopent[a]-anthracene-6,11-dione (208 mg, 61%), is obtained after filtration and dried, mp 225°-230° C. The compound is used directly in the next step without further purification. 1H NMR (CDCl3): δ2.22 (2H, dt, J=7.14 Hz, J=7.69 Hz, CH2 -2), 3.06 (2H, t, J=7.14 Hz, CH2 -3), 3.53 (2H, t, J=7.69 Hz, CH2 -1), 4.54 (2H, s, CH2 --S), 7.22-8.37 (5H, m, Ar--H).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4.5 hours under nitrogen
  3. temperatureAfter cooling
  4. washthe mixture is washed with H2O (20 mL×3)
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo to dryness
  7. additionThe residue is then treated with boiling ethyl ether for 10 minutes
  8. customstored in the refrigerator overnight

Sources & evidence

ORD record
ord-23d1bf8c804345bdaa03a5816a75460d
Source dataset
uspto-grants-1995_12
Patent number
US05476952

Reaction notes

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