Methanol → HCID 19864332, compound

HRID 1199930Notes

Reaction equation

HRID 1199930 reaction equation
[Cu][C:2]#[N:3].Br[C:5]1[C:14]2[CH2:13][CH2:12][N:11]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:10][CH:9]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:8]=2[S:7][CH:6]=1.CO>CN(C)C=O>[C:21]1([CH:9]2[C:8]3[S:7][CH:6]=[C:5]([C:2]#[N:3])[C:14]=3[CH2:13][CH2:12][N:11]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:10]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 19864310HCID 19864310, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 19864332HCID 19864332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of copper (I) cyanide (0.45 g) and 3-bromo-8-phenyl-5,6,7,8-tetrahydro-6-trifluoroacetyl-4H-thieno[2,3-d]azepine (1.0 g) in dry dimethylformamide (10 ml) was heated under reflux for 5 hours. After allowing to cool to room temperature methanol (35 ml) was added and the mixture stirred vigorously, filtered and the filtrate evaporated to a yellow oil. Chromatography on silica eluting with diethylether gave the nitrile product, m.p. 107°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. additionwas added
  4. filtrationfiltered
  5. customthe filtrate evaporated to a yellow oil

Sources & evidence

ORD record
ord-febb7bd0d23e4e6aab1153a81845c28f
Source dataset
uspto-grants-1990_02
Patent number
US04904653

Reaction notes

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