Morpholine → 4-Morpholinecarbothioamide

HRID 885900Notes

Reaction equation

HRID 885900 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=[CH:9]1)([N:3]1C=CN=C1)=[S:2].N1CC[O:16][CH2:15]C1>C1COCC1>[N:8]1([C:1](=[S:2])[NH2:3])[CH2:12][CH2:11][O:16][CH2:15][CH2:9]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 23935444-MorpholinecarbothioamideYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,1′-thiocarbonyldiimidazole (10.0 g, 56.1 mmol) in THF (150 mL) was added morpholine (4.2 g, 4.2 mL, 48.7 mmol). The reaction mixture was then stirred for 72 h at r.t. before it was concentrated in vacuo to 30 mL and NH3 (60.0 mL, 2.0M in MeOH) was added. The reaction mixture was stirred at r.t. in a sealed flask for 18 h, filtered and the resultant solid washed with Et2O to give the title compound (2.0 g, 28%) as a white solid that was used without further purification. δH (DMSO-d6) 7.46 (2H, br. s), 3.82-3.61 (4H, m), 3.60-3.53 (4H, m).

Workup

  1. concentrationwas concentrated in vacuo to 30 mL and NH3 (60.0 mL, 2.0M in MeOH)
  2. additionwas added
  3. stirringThe reaction mixture was stirred at r.t. in a sealed flask for 18 h
  4. filtrationfiltered
  5. washthe resultant solid washed with Et2O

Sources & evidence

ORD record
ord-d0088899afad4a9db668a75e7f0446da
Source dataset
uspto-grants-2012_08
Patent number
US08242116B2

Reaction notes

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