Water →
Reaction equation
[CH2:1]([CH:3]1O[CH2:4]1)[Cl:2].[S-:6]C#N.[NH4+].[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.O>C1(C)C=CC=CC=1>[N:10]1[CH:15]=[CH:14][CH:13]=[CH2+:12][CH:11]=1.[Cl-:2].[S:6]1[CH2:4][CH2:3][CH2:1]1Participants
5
Reactant 4
Product 0
No Product data yet.
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of epichlorohydrin (5.34 g) in toluene (60 mL) were added ammonium thiocyanate (9.1 g), pyridine (23.7 g) and water (60 mL). The resulting mixture was stirred at 50° C. for 16 h. The two phases were separated and the aqueous phase was then lyophilized to give a yellow oil (11.4 g). The crude oil was filtered over a plug of silica gel, eluting with EtOH:H2O (100:0 to 95:5). The desired salt was obtained as an amber solid was obtained (5.3 g). 1H-NMR (D2O, 500 MHz): 3.59 (t, 2H), 3.91 (t, 2H), 5.99 (dt, 2H), 8.00 (m, 2H), 8.47 (m, 1H), 8.86 (m, 2H). 13C-NMR (D2O, 125 MHz): 32.6 (2C), 63.8, 128.1 (2C), 141.7, 146.5 (2C).
Workup
- customThe two phases were separated
Sources & evidence
- ORD record
- ord-eddb47b0a6604c21a3db95e14569718d
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09006456B2
Reaction notes
Loading…