Dimethylformamide → HCID 13151854, compound

HRID 485420Notes

Reaction equation

HRID 485420 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:17]=1.[CH3:18][N:19](C)C=O>>[C:18]([C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[S:7][C:6]=2[CH:17]=1)#[N:19]

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 13151853HCID 13151853, compound

Product 1

HCID 13151854HCID 13151854, compound

Procedure

36.45 G. 3-bromo-10,11-dihydro-11-oxodibenzo[b,f]thiepin and 32.11 g. cuprous cyanide are refluxed in 450 cc. dimethylformamide for five and one half hours. The reaction mixture is cooled down and poured into 2 l. of ice water with good mechanical stirring. The resulting solid is filtered, washed with water, then extracted into 1.7 l. chloroform. The insoluble copper salts are filtered and the filtrate evaporated to dryness. The residue is triturated in methanol and the insoluble yellow product is filtered and weighs 22.4 g. (74.6%), m.p. 166°-170° C.

Workup

  1. temperatureThe reaction mixture is cooled down
  2. additionpoured into 2 l
  3. filtrationThe resulting solid is filtered
  4. washwashed with water
  5. extractionextracted into 1.7 l
  6. filtrationThe insoluble copper salts are filtered
  7. customthe filtrate evaporated to dryness
  8. customThe residue is triturated in methanol
  9. filtrationthe insoluble yellow product is filtered

Sources & evidence

ORD record
ord-dc99f5b8136d4dacb011f347f2b02917
Source dataset
uspto-grants-1985_08
Patent number
US04536507

Reaction notes

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