Thiomorpholine → Thiomorpholine-4-carboxamide

HRID 2100422Notes

Reaction equation

HRID 2100422 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.C[Si]([N:11]=[C:12]=[O:13])(C)C>C(O)(C)C>[N:1]1([C:12]([NH2:11])=[O:13])[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 67164ThiomorpholineHCID 70696Trimethylsilyl isocyanate

Product 1

HCID 12517904Thiomorpholine-4-carboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of thiomorpholine (1.0 g, 9.7 mmol) in isopropanol (25 mL) at rt was added trimethylsilylisocyanate (1.9 mL, 13.45 mmol) and the resulting solution stirred overnight. The resulting suspension was filtered and the filtrate concentrated in vacuo to give thiomorpholine-4-carboxylic acid amide (1.18 g, 89%); 1H-NMR (300 MHz, d6-DMSO) 6.00 (2H, s), 3.53-3.57 (4H, m), 2.46-2.51 (4H, m, obscured by solvent).

Workup

  1. filtrationThe resulting suspension was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-aea0ae312d214113bfb7d37ead8876be
Source dataset
uspto-grants-2009_08
Patent number
US07572794B2

Reaction notes

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