HCID 86701454, compound → HCID 86701455, compound

HRID 2173916Notes

Reaction equation

HRID 2173916 reaction equation
[CH3:1][C:2]1[C:9]([N+:10]([O-])=O)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([S:13][CH3:14])[CH:3]=1.[CH:15]([Mg]Br)=[CH2:16]>C1COCC1>[CH3:1][C:2]1[C:9]2[NH:10][CH:16]=[CH:15][C:8]=2[C:5]([C:6]#[N:7])=[C:4]([S:13][CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 86701454HCID 86701454, compoundHCID 178418507HCID 178418507, compound

Product 1

HCID 86701455HCID 86701455, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-methyl-2-(methylthio)-5-nitrobenzonitrile (1.6 g, 7.68 mmol) in THF (80 mL) at −78° C. under nitrogen, was added rapidly 1M vinylmagnesium bromide in THF (30.7 mL, 30.7 mmol). After addition was complete, the reaction was stirred at −78° C. for 30 min. The reaction was then quenched with sat. aq. NH4Cl and extracted with EtOAc. The organic extract was dried over MgSO4, filtered and concentrated. The pure title compound was isolated using FCC (0-50% EtOAc in heptanes). MS (ESI−) m/z 201.2 (M−H).

Workup

  1. additionAfter addition
  2. customThe reaction was then quenched with sat. aq. NH4Cl
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0fb2a24242004d4f9406620099e63a85
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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