Methanol → HCID 70655759, compound

HRID 2368038Notes

Reaction equation

HRID 2368038 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:7][CH2:6][C:5]([C:8]2[C:9]([NH:14][C:15]([NH:17]C(OCC)=O)=S)=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH2:3]1.Cl.[NH2:25]O.CO>C(O)C>[CH3:23][C:2]1([CH3:1])[CH2:7][CH2:6][C:5]([C:8]2[C:9]3[N:10]([N:25]=[C:15]([NH2:17])[N:14]=3)[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 86670236HCID 86670236, compound

Product 1

HCID 70655759HCID 70655759, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of N-[3-(4,4-dimethyl-cyclohex-1-enyl)-pyridin-2-yl]-N′-carboethoxy-thiourea (1.42 g, 3.48 mmol) in ethanol (4.3 mL) was added at room temperature hydroxylamine hydrochloride (1.50 g, 21.4 mmol) and methanol (4.3 mL). The yellow suspension was heated to 70° C. over night. The solvent was evaporated under reduced pressure and the residue was partitionated between ethyl acetate and water. The aqueous layer was extracted twice with ethyl acetate and the organic layers were combined, washed with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was removed under reduced pressure. The crude material was purified by column chromatography on silica gel first with ethyl acetate as the eluent and then once again with a mixture of heptane/ethyl acetate (1:1 v/v) as the eluent to yield the title compound as a yellow solid (526 mg, 51%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe crude material was purified by column chromatography on silica gel first with ethyl acetate as the eluent
  8. additiononce again with a mixture of heptane/ethyl acetate (1:1 v/v) as the eluent

Sources & evidence

ORD record
ord-cf39ca441dfe4f80a74f53b6d75951e6
Source dataset
uspto-grants-2014_04
Patent number
US08703763B2

Reaction notes

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