Potassium Cyanide → HCID 54307398, compound

HRID 2269581Notes

Reaction equation

HRID 2269581 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[C:9]=1[CH2:10]Br)=[O:4].COC(C1SC(C2C=CC(F)=CC=2)=C(C2C=CC(SC)=CC=2)C=1CBr)=O.FC1C=CC(C=O)=CC=1.[C-:61]#[N:62].[K+]>CS(C)=O.O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[C:9]=1[CH2:10][C:61]#[N:62])=[O:4]

Participants

7

Reactant 4

HCID 9032Potassium CyanideHCID 680234-FluorobenzaldehydeHCID 54071145HCID 54071145, compoundHCID 54283396HCID 54283396, compound

Product 1

HCID 54307398HCID 54307398, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To 3-bromomethyl-4-(4-(methylthio)phenyl)-5-phenyl-thiophene-2-carboxylic acid methyl ester (1 g, prepared by using the same procedure described for 3-bromomethyl-5-(fluorophenyl)-4-(4-(methylthio)phenyl)thiophene-2-carboxylic acid methyl ester of Example 8, Step 2 but substituting benzaldehyde for 4-fluorobenz-aldehyde) in DMSO (25 mL) in an ice bath was added powdered KCN. The mixture was stirred for 15 minutes at R.T., then H2O was added and the mixture was extracted with Et2O (2X), the organic layers were combined, washed with brine, dried over MgSO4, filtered and the solvent was evaporated under vacuum. Purification by silica gel chromatography afforded the title compound.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with Et2O (2X)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated under vacuum
  7. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-2b12f7adc78d45a3996c8662e8d28778
Source dataset
uspto-grants-2001_12
Patent number
US06329421B1

Reaction notes

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