Reaction equation
[C-:1]#[N:2].[Na+].Cl.[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][CH2:11][NH2:12].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH:16]=O>O.C(O)C>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][CH2:11][NH:12][CH:16]([C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[Cl:13])[C:1]#[N:2]Participants
Conditions
- Temperature
- 45 °C
Procedure
9,8 g (0,2 mol) of sodium cyanide is dissolved in 70 ml of water and to the solution first 32,8 g (0,2 mol) of 2-(2-thienyl)ethylamine hydrochloride, then in a period of a few minutes, the solution of 28,2 g (0,2 mol) of o-chlorobenzaldehyde in 30 ml of ethanol are added. During the addition the temperature of the mixture raises to 45° C. The reaction mixture is then stirred at 60° C. for 2 hours, then cooled to room temperature and diluted with 50 ml of water. The resulting oily product is extracted with 100 ml of 1,2-dichloroethane, the organic phase is washed to cyanide-free with 2×50 ml of water, the traces of 2-(2-thienyl)ethylamine are removed by treatment with 20 ml of 3% hydrochloric acid solution. The residual fast crystallizing oil is the product. Weight: 52 g (94%) mp.: 40-41° C. The product was identified as written in Example 1. Quality of the product is identical to that of the product prepared according to Example 1.
Workup
- waitin a period of a few minutes
- additionDuring the addition the temperature of the mixture
- temperaturecooled to room temperature
- extractionThe resulting oily product is extracted with 100 ml of 1,2-dichloroethane
- washthe organic phase is washed to cyanide-free with 2×50 ml of water
- customthe traces of 2-(2-thienyl)ethylamine are removed by treatment with 20 ml of 3% hydrochloric acid solution
- customThe residual fast crystallizing oil
- customprepared
Sources & evidence
- ORD record
- ord-f7b42af54d424ed99d8dcad315ece46e
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06670486B1
Linked notes
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