1,4-Dioxaspiro[4.5]decane-8-carbonitrile → 1,4-Dioxaspiro[4.5]decane-8-carbothioamide

HRID 1930059Notes

Reaction equation

HRID 1930059 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[NH4+]=[S:14]>CO>[O:1]1[C:5]2([CH2:10][CH2:9][CH:8]([C:11](=[S:14])[NH2:12])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 111164331,4-Dioxaspiro[4.5]decane-8-carbonitrile

Product 1

HCID 579299251,4-Dioxaspiro[4.5]decane-8-carbothioamideYield 23%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 1,4-dioxaspiro[4.5]decane-8-carbonitrile (1.16 g, 6.94 mmol, Tetrahedron, 2002, 58(8), 1557), ammonium sulfide (20 wt. % in water, 2.84 mL, 8.33 mmol) and MeOH (14 mL) were heated in a CEM® microwave at about 130° C. for about (250 psi maximum pressure, 10 min ramp, 300 max watts). The mixture was concentrated under a stream of air and the resulting material was purified by flash chromatography on silica gel using EtOAc/heptane (7:3) as an eluent to give the title compound (0.317 g, 23%) as a light yellow solid: LC/MS (Table 1, Method a) Rt=1.68 min; MS m/z: 202.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under a stream of air
  2. customthe resulting material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-e6fd7324118d440d8eb1e3cb075d0f27
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

Loading…