Iodine → HCID 178501075, compound

HRID 1893353Notes

Reaction equation

HRID 1893353 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11](=S)[NH2:12])[CH2:7][CH2:6]1)=[O:4].[C:14]([NH2:17])(=[S:16])[CH3:15].II>CO>[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]2[N:17]=[C:14]([CH3:15])[S:16][N:12]=2)[CH2:7][CH2:6]1)=[O:4]

Participants

5

Reactant 3

HCID 807IodineHCID 2723949ThioacetamideHCID 178501132HCID 178501132, compound

Product 1

HCID 178501075HCID 178501075, compoundYield 5.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of trans-4-thiocarbamoyl-cyclohexanecarboxylic acid methyl ester (0.30 g, 1.5 mmol) and thioacetamide (0.67 g, 8.9 mmol) in methanol (7 ml) was added a solution of iodine (2.65 g, 10.4 mmol) in methanol (15 ml) at room temperature. After stirring for 48 h the reaction mixture was partitioned between 0.1 M sodium thiosulfate solution (100 ml) and ethyl acetate (100 ml). The layers were separated. The aqueous layer was extracted with two 50-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by Kugelrohr distillation. The distillate was purified by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent to give the title compound (0.021 g, 5%) as light yellow oil, which was contaminated with 20% trans-4-(3-methyl-[1,2,4]thiadiazol-5-yl)-cyclohexanecarboxylic acid methyl ester. MS m/e: 241 ([M+H]+)

Workup

  1. customwas partitioned between 0.1 M sodium thiosulfate solution (100 ml) and ethyl acetate (100 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with two 50-ml portions of ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. distillationThe residue was purified by Kugelrohr distillation
  7. distillationThe distillate was purified by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent

Sources & evidence

ORD record
ord-f83420bf11514355a9ac86f4e0710e48
Source dataset
uspto-grants-2013_08
Patent number
US08513238B2

Reaction notes

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