Dichloromethane → 2-Methylcyclohexanecarbonyl chloride

HRID 2204508Notes

Reaction equation

HRID 2204508 reaction equation
C1N=CN(C(N2C=N[CH:10]=[CH:9]2)=O)C=1.[O:13]1[CH2:18][CH2:17]OCC1.[CH2:19]1[CH2:23]O[CH2:21][CH2:20]1.C(Cl)[Cl:25]>N1C=CC=CC=1.CN(C=O)C>[CH3:9][CH:10]1[CH2:23][CH2:19][CH2:20][CH2:21][CH:17]1[C:18]([Cl:25])=[O:13]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 312751,4-DioxaneHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 27598372-Methylcyclohexanecarbonyl chloride

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent3×HCID 6228DimethylformamideSolvent

Procedure

To a flask containing an amine or an amine salt (preferably 1 equiv) is added CDI (1-2 equiv, preferably 1.10 equiv) and an organic solvent (such as 1,4-dioxane, THF, DCM, DMF, or pyridine, preferably pyridine). If an amine salt is used, pyridine is used as the solvent. The reaction mixture is stirred at ambient temperature for about 2-24 h (preferably about 16 h). A second amine (1-3 equiv, preferably 1.10 equiv) is then added to the mixture which is stirred at ambient temperature for about 2-24 h (preferably about 16 h). The organic solvent is optionally removed under reduced pressure. The crude material can be partitioned between an organic solvent (such as EtOAc or DCM) and water, an aqueous base (such as saturated aqueous NaHCO3) or brine. The layers are separated and the organic solution is optionally washed with water, an aqueous base (such as saturated aqueous NaHCO3) and/or brine, dried over anhydrous Na2SO4 or MgSO4, filtered, and concentrated under reduced pressure to give the target compound. The crude material is optionally purified by precipitation, crystallization, or trituration from an appropriate solvent or solvents or by chromatography to give the target compound.

Workup

  1. stirringis stirred at ambient temperature for about 2-24 h (preferably about 16 h)
  2. customThe organic solvent is optionally removed under reduced pressure
  3. customThe crude material can be partitioned between an organic solvent (such as EtOAc or DCM) and water
  4. customThe layers are separated
  5. washthe organic solution is optionally washed with water
  6. dry with materialan aqueous base (such as saturated aqueous NaHCO3) and/or brine, dried over anhydrous Na2SO4 or MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give the target compound
  10. customThe crude material is optionally purified by precipitation, crystallization, or trituration from an appropriate solvent or solvents or by chromatography
  11. customto give the target compound

Sources & evidence

ORD record
ord-1b34a4b8c464424295c3cfd248a4c459
Source dataset
uspto-grants-2016_06
Patent number
US09365579B2

Reaction notes

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