Dimethylformamide → HCID 13151854, compound

HRID 1074983Notes

Reaction equation

HRID 1074983 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-d9231dfb908c4d49b2d49e4a572462de
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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