Ammonia → 4-Aminothiane-4-carbonitrile

HRID 1504812Notes

Reaction equation

HRID 1504812 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=O)[CH2:3][CH2:2]1.[NH3:8].C[Si](C)(C)[C:11]#[N:12]>C(O)C>[NH2:8][C:4]1([C:11]#[N:12])[CH2:5][CH2:6][S:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 66173Tetrahydrothiopyran-4-oneHCID 82115Trimethylsilyl cyanide

Product 1

HCID 158187404-Aminothiane-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tetrahydro-4H-thiopyran-4-one (215 g, 1.85 mol) in ethanol (1500 mL) was bubbled ammonia gas at 0° C. After 4 hours, trimethylsilanecarbonitrile (184 g, 1.86 mol) was added dropwise and then the reaction mixture was allowed to warm to ambient temperature. After 5 hours, the reaction mixture was concentrated under reduced pressure and then diluted with hexane (800 mL). The mixture was filtered, and the solids were washed with hexanes (2×400 mL) and dried under reduced pressure to afford 4-aminotetrahydro-2H-thiopyran-4-carbonitrile. The material was used without further purification.

Workup

  1. waitAfter 5 hours
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additiondiluted with hexane (800 mL)
  4. filtrationThe mixture was filtered
  5. washthe solids were washed with hexanes (2×400 mL)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-fb4f173a0bb14719a0e89199cc17542c
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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