Pyridine → HCID 178501062, compound

HRID 1893351Notes

Reaction equation

HRID 1893351 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=[S:18])[N:12]=[C:13]([N:15](C)C)[CH3:14])[CH2:7][CH2:6]1)=[O:4].N1C=CC=CC=1.NOS(O)(=O)=O>C(O)C.CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[S:18][N:15]=[C:13]([CH3:14])[N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 178501169HCID 178501169, compound

Product 1

HCID 178501062HCID 178501062, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of trans-4-[1-dimethylamino-ethylidenethiocarbamoyl]-cyclohexanecarboxylic acid methyl ester (0.87 g, 3.2 mmol) and pyridine (0.52 ml, 6.5 mmol) in ethanol (6 ml) was added a solution of hydroxylamine-O-sulfonic acid (0.45 g; 3.6 mmol) in methanol (3 ml) at room temperature. After stirring over night the reaction mixture was partitioned between 1 M aqueous hydrochloric acid solution (100 ml) and ethyl acetate (100 ml). The layers were separated. The aqueous layer was extracted with one 100-ml portion of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.68 g, 88%) as yellow oil. MS m/e: 241 ([M+H]+)

Workup

  1. customwas partitioned between 1 M aqueous hydrochloric acid solution (100 ml) and ethyl acetate (100 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with one 100-ml portion of ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7edb74d28ef640f99b233362f9f90c63
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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