Methane → HCID 13812588, compound

HRID 1650703Notes

Reaction equation

HRID 1650703 reaction equation
[CH3:1][C:2](=[N:4]O)[CH3:3].[C:6](Cl)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][CH:8]=1.CCOCC.C>N>[CH3:1][C:2]1[N:4]=[C:6]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)[O:13][CH:3]=1

Participants

6

Reactant 4

HCID 297MethaneHCID 3283Diethyl EtherHCID 67180Acetone, oximeHCID 82604Nicotinoyl chloride

Product 1

HCID 13812588HCID 13812588, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Conditions

Temperature
120 °C

Procedure

To 10 g (0.140 mol) of acetone oxime cooled to -10° C. neat nicotinoyl chloride (40 g, 0.280 mol) was added dropwise under a nitrogen atmosphere. A violent reaction occured and the mixture became quickly solid. The solid was heated to 120° C. for 3 h. After cooling the mixture was dissolved in ice water and ammonia. After addition of 300 ml of ether the mixture was treated with charcoal, filtered, and the ether phase separated. The aqueous phase was extracted with 2×200 ml of ether, and the combined organic phase dried over magnesium sulphate. Removal of solvent in vacuo gave crude 82 as a red oil. Yield: 3.9 g (0.024 mol, 17%).

Workup

  1. additionwas added dropwise under a nitrogen atmosphere
  2. customA violent reaction
  3. temperatureAfter cooling the mixture
  4. filtrationfiltered
  5. customthe ether phase separated
  6. extractionThe aqueous phase was extracted with 2×200 ml of ether
  7. dry with materialthe combined organic phase dried over magnesium sulphate
  8. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-d23ff6c8c8104fb2a1a704bec48640d1
Source dataset
uspto-grants-1990_05
Patent number
US04925858

Reaction notes

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