Hydrogen Sulfide → 4-(1,3-Dioxolan-2-yl)benzene-1-carbothioamide

HRID 735987Notes

Reaction equation

HRID 735987 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[SH2:14]>N1C=CC=CC=1.O>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10](=[S:14])[NH2:11])=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 402Hydrogen SulfideHCID 27784284-(1,3-Dioxolan-2-yl)benzonitrile

Product 1

HCID 27787314-(1,3-Dioxolan-2-yl)benzene-1-carbothioamideYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of 4-(1,3-dioxolan-2-yl)benzonitrile (2 g, 0.01 mol) in dry pyridine (50 mL) and TEA (5.75 g, 0.057 mol) was passed H2S gas (freshly generated) for 1 h with stirring at RT. The reaction mixture was diluted with water (100 mL), extracted with diethyl ether (100 mL), washed with brine (50 mL) and dried. The solvent was removed under vacuum and the crude product was purified by column chromatography over silica gel (PetEther/EtOAc, 3/7) to give 4-(1,3-dioxolan-2-yl)benzenecarbothioamide (1.9 g, 86%) as yellow solid. TLC (PetEther/EtOAc 3/7), Rf=0.35

Workup

  1. customfor 1 h
  2. extractionextracted with diethyl ether (100 mL)
  3. washwashed with brine (50 mL)
  4. customdried
  5. customThe solvent was removed under vacuum
  6. customthe crude product was purified by column chromatography over silica gel (PetEther/EtOAc, 3/7)

Sources & evidence

ORD record
ord-fa411c6870b34f6483c1b24b4d3a4155
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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