HCID 13151860, compound → HCID 13490401, compound

HRID 1074992Notes

Reaction equation

HRID 1074992 reaction equation
BrC1C=CC2CCC3C=CC=CC=3SC=2C=1.[CH:17]1[C:27]2[CH2:26][CH2:25][C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[S:22][C:21]=2[CH:20]=[C:19]([C:32]([NH2:34])=O)[CH:18]=1>CN(C)C=O>[C:32]([C:19]1[CH:18]=[CH:17][C:27]2[CH2:26][CH2:25][C:24]3[CH:28]=[CH:29][CH:30]=[CH:31][C:23]=3[S:22][C:21]=2[CH:20]=1)#[N:34]

Participants

4

Reactant 2

HCID 13151860HCID 13151860, compoundHCID 13151861HCID 13151861, compound

Product 1

HCID 13490401HCID 13490401, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.61 G. 3-bromo-10,11-dihydrodibenzo[b,f]thiepin and 4.3 g. cuprous cyanide are refluxed in 50 cc. dimethylformamide for 51/2 hours. The mixture is poured onto ice and the solid filtered. The solid is triturated with chloroform and filtered. The chloroform is evaporated to yield 4.5 g. residue which is chromatographed on silica gel. Elution with benzene affords 2.83 g. (75.4%) of the desired pure oily compound which crystallizes on standing. Elution with ethyl acetate gives 440 mg. 10,11-dihydrodibenzo[b,f]thiepin-3-carboxylic acid amide as a white solid, m.p. 145°-147° C.

Workup

  1. custom2 hours
  2. additionThe mixture is poured onto ice
  3. filtrationthe solid filtered
  4. customThe solid is triturated with chloroform
  5. filtrationfiltered
  6. customThe chloroform is evaporated
  7. customto yield 4.5 g
  8. customresidue which is chromatographed on silica gel
  9. washElution with benzene
  10. customaffords 2.83 g
  11. custom(75.4%) of the desired pure oily compound which crystallizes
  12. washElution with ethyl acetate
  13. customgives 440 mg

Sources & evidence

ORD record
ord-fe5c66d97c484bb9bc8da0e676ec7a4f
Source dataset
uspto-grants-1983_07
Patent number
US04394515

Reaction notes

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