Hydrazinecarbothioamide, N-phenyl- → HCID 86743980, compound

HRID 1651670Notes

Reaction equation

HRID 1651670 reaction equation
[CH:1]([CH:3]1[CH:8]([CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:7][O:6][CH:5]([CH3:19])[O:4]1)=O.[C:20]1([NH:26][C:27](=[S:30])[NH:28][NH2:29])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(O)C.C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:18][O:17][C:15]([CH2:14][CH2:13][CH2:12]/[CH:11]=[CH:10]\[CH2:9][C@H:8]1[CH2:7][O:6][C@@H:5]([CH3:19])[O:4][C@H:3]1[CH:1]=[N:29][NH:28][C:27]([NH:26][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[S:30])=[O:16]

Participants

6

Reactant 2

HCID 730679Hydrazinecarbothioamide, N-phenyl-HCID 86743981HCID 86743981, compound

Product 1

HCID 86743980HCID 86743980, compoundYield 114.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of 2R,4R, 5S)-4-formyl-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-1,3-dioxane (62 mg) and 4-phenyl-3-thiosemicarbazide (46 mg) in ethanol (2 ml) was added acetic acid (1 drop) and the solution was stirred at room temperature for 4 hours. The mixture was diluted with chloroform (15 ml) and the solution was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo to give (2R,4R,5S)-5-[(Z)-6-methoxycarbonyl-2-hexenyl]-2-methyl-4-[4-(phenyl)thiosemicarbazonomethyl]-1,3-dioxane (110 mg) as an oil.

Workup

  1. washthe solution was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-5eefbcdf306d45b198f3dd66c6ebcd80
Source dataset
uspto-grants-1990_05
Patent number
US04929639

Reaction notes

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