Methyl isothiocyanate → HCID 86677610, compound

HRID 1484449

Reaction equation

HRID 1484449 reaction equation
[CH2:1]1[C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:4][N:3]=[N:2]1.[CH3:11][N:12]=[C:13]=[S:14]>C(O)C>[CH3:11][NH:12][C:13]([N:2]1[N:3]=[CH:4][C:5]2([CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)[CH2:1]1)=[S:14]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 593394748-Oxa-2,3-diaza-spiro[4,5]dec-2-ene

Product 1

HCID 86677610HCID 86677610, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.8 g (1 mol equiv.) 8-Oxa-2,3-diaza-spiro[4.5]dec-2-ene (synthesized as described in WO 2008/034863) and 0.54 g (1.3 mol equiv.) methyl isothiocyanate were added to 10 mL ethanol, and the reaction mixture was refluxed for 5 hours. Silica gel was added and volatiles were removed under reduced pressure. Purification by flash chromatography on silica gel (Et2O) afforded 0.52 g (35%) 8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carbothioic acid methylamide. 1H NMR (400 MHz, CDCl3) δ 1.52-1.59 (m, 3H), 1.82-1.90 (m, 2H), 3.17 (d, J=5.0, 3H), 3.56-3.64 (m, 2H), 3.86-3.92 (m, 2H), 4.11 (s, 2H), 6.80 (s, 1H), 7.21 (br.s., 1H).

Workup

  1. temperaturethe reaction mixture was refluxed for 5 hours
  2. additionSilica gel was added
  3. customvolatiles were removed under reduced pressure
  4. customPurification by flash chromatography on silica gel (Et2O)

Sources & evidence

ORD record
ord-1df0a8c9399144d5a76ef8e47af25d19
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Linked notes

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