Reaction equation
[CH2:1]([NH:3][C:4]([N:6]1[N:10]=[CH:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:7]1)=[S:5])[CH3:2].I[CH3:16]>CO>[CH3:16][S:5][C:4]([N:6]1[N:10]=[CH:9][C:8]2([CH2:14][CH2:13][CH2:12][CH2:11]2)[CH2:7]1)=[N:3][CH2:1][CH3:2]Participants
4
Conditions
- Temperature
- 45 °C
Procedure
0.55 g (1 mol equiv.) 2,3-Diazaspiro[4.4]non-3-ene-2-carbothioic acid ethylamide was dissolved in 15 mL MeOH, 3.4 mL (21 mol equiv.) iodomethane was added and the magnetically stirred reaction mixture was heated at 45° C. for 2 hours. Volatiles were removed in vacuo. The residue was taken up in dichloromethane (DCM) and extracted with 5% aqueous NaHCO3. The organic layer was washed twice with water, dried over Na2SO4, filtered and evaporated to dryness to give 0.57 g (97%) N-ethyl-2,3-diaza-spiro[4.4]non-3-ene-2-carboximidothioic acid methyl ester. 1H NMR (400 MHz, CDCl3) δ 1.16 (t, J=7.3 Hz, 3H), 1.64-1.80 (m, 8H), 2.46 (s, 3H), 3.54 (q, J=7.3 Hz, 2H), 3.57 (s, 2H), 6.72 (s, 1H).
Workup
- customthe magnetically stirred reaction mixture
- customVolatiles were removed in vacuo
- extractionextracted with 5% aqueous NaHCO3
- washThe organic layer was washed twice with water
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-6a9e51a789234d63b6480ba20ec75e6f
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422244B2
Linked notes
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