Chloroform → HCID 12929159, compound

HRID 894181Notes

Reaction equation

HRID 894181 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][O:10][C:9]3[CH:12]=[C:13]4[O:18][CH2:17][O:16][C:14]4=[CH:15][C:8]=3[C:7](=[O:19])[C:6]=2[CH:20]=1.[CH3:21][N:22](C)C=O.C(Cl)(Cl)Cl.[C-]#N.[Na+]>O>[CH2:17]1[O:18][C:13]2[C:14](=[CH:15][C:8]3[C:7](=[O:19])[C:6]4[CH:20]=[C:2]([C:21]#[N:22])[CH:3]=[CH:4][C:5]=4[CH2:11][O:10][C:9]=3[CH:12]=2)[O:16]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 12929160HCID 12929160, compound

Product 1

HCID 12929159HCID 12929159, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Heat a mixture of 9.26 gm. (0.0278 mole) of 9-bromo-6,11-dihydro-2,3-methylenedioxy-11-oxodibenz[b,e]oxepin, 5.23 (0.0584 mole) of cuprous cyanide and 33 ml. of dimethylformamide under reflux for 9 hours with vigorous stirring. Cool the reaction mixture and shake with a mixture of 45 ml. of chloroform, 32 ml. of saturated sodium cyanide solution and 32 ml. of water until all solids have dissolved. Separate the organic layer, wash with aqueous sodium cyanide solution and water and dry over anhydrous magnesium sulfate. Remove the solvent under vacuum to obtain the title product (yield 7.76 gm., m.p. 217°-220° C.). Recrystallize from acetic acid to obtain pure product as tan prisms [m.p. 224°-225° C., pmr (CDCl3) 5.03 (2H,s, CH2O), 617(2H,s,OCH2O--)].

Workup

  1. temperatureHeat
  2. additiona mixture of 9.26 gm
  3. temperatureCool the reaction mixture and shake
  4. additionwith a mixture of 45 ml
  5. customSeparate the organic layer
  6. washwash with aqueous sodium cyanide solution and water
  7. dry with materialdry over anhydrous magnesium sulfate
  8. customRemove the solvent under vacuum

Sources & evidence

ORD record
ord-78392aee24f3491ca39debaa51d68a8b
Source dataset
uspto-grants-1981_08
Patent number
US04282365

Reaction notes

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