Methyl iodide → N-methyl-8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carboximidothioic acid methyl ester

HRID 1484450Notes

Reaction equation

HRID 1484450 reaction equation
[CH3:1][NH:2][C:3]([N:5]1[N:9]=[CH:8][C:7]2([CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:6]1)=[S:4].I[CH3:16]>CO>[CH3:16][S:4][C:3]([N:5]1[N:9]=[CH:8][C:7]2([CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH2:6]1)=[N:2][CH3:1]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86677610HCID 86677610, compound

Product 1

HCID 67360788N-methyl-8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carboximidothioic acid methyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

0.50 g (1 mol equiv.) 8-Oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carbothioic acid methylamide was dissolved in 10 mL methanol; 1.2 mL (10 mol equiv.) iodomethane was added and the reaction mixture was heated at 50° C. for 5 hours. Volatiles were removed under reduced pressure, and the residue was taken up in DCM and extracted with 5% aqueous NaHCO3. The organic layer was washed twice with water, dried over Na2SO4, filtered and evaporated to dryness to yield 0.43 g (99%) N-methyl-8-oxa-2,3-diaza-spiro[4.5]dec-3-ene-2-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 1.53-1.60 (m, 2H), 1.80-1.88 (m, 2H), 2.47 (s, 3H), 3.26 (s, 3H), 3.56-3.64 (m, 2H), 3.68 (s, 2H), 3.83-3.89 (m, 2H), 6.73 (s, 1H).

Workup

  1. customVolatiles were removed under reduced pressure
  2. extractionextracted with 5% aqueous NaHCO3
  3. washThe organic layer was washed twice with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-eba4ecaca9d048fda4adda20386843c7
Source dataset
uspto-grants-2016_08
Patent number
US09422244B2

Reaction notes

Loading…