Triethylamine → HCID 14929112, compound

HRID 2213329Notes

Reaction equation

HRID 2213329 reaction equation
O[CH:2]([C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])[CH2:3][N+:4]([O-:6])=[O:5].C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[N+:4](/[CH:3]=[CH:2]/[C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[C:10]#[N:11])([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11355984HCID 11355984, compound

Product 1

HCID 14929112HCID 14929112, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-(1-Hydroxy-2-nitroethyl)benzonitrile (3.32 g, 17.3 mmol) and triethylamine (4.37 g, 43.2 mmol) were stirred in anhydrous dichloromethane (100 mL) at 0° C. To the resulting solution was added methanesulfonyl chloride (2.77 g, 24.2 mmol) dropwise via syringe, after which time the reaction was warmed to ambient temperature and stirred for 15 min. The resulting reaction mixture was diluted with additional dichloromethane (200 mL) and partitioned with H2O (100 mL). The dichloromethane layer was dried (MgSO4), filtered and concentrated in vacuo. The resulting crude residue was filtered through silica gel eluting with hexane:EtOAc (4:1) to afford 3-[(E)-2-nitroethenyl]benzonitrile as a yellow solid.

Workup

  1. customThe resulting reaction mixture
  2. custompartitioned with H2O (100 mL)
  3. dry with materialThe dichloromethane layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. filtrationThe resulting crude residue was filtered through silica gel eluting with hexane:EtOAc (4:1)

Sources & evidence

ORD record
ord-acf789a1adf24da89f0ac1000155170e
Source dataset
uspto-grants-2006_09
Patent number
US07105548B2

Reaction notes

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