2-(Oxiran-2-ylmethoxy)benzonitrile → N-2-[(3-(2-cyanophenoxy)-2-hydroxypropyl)amino]ethyl-N'-(3,5-dimethoxyphenyl)thiourea
Reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[N:12].[NH2:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[CH:22]=1)=[S:19]>C(O)(C)C>[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH:2]([OH:1])[CH2:13][NH:14][CH2:15][CH2:16][NH:17][C:18]([NH:20][C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[CH:22]=1)=[S:19])#[N:12]Participants
Procedure
A solution of 1.28 g (7.3 mmoles) of 2,3-epoxy-1-(2-cyanophenoxy)propane, 7, in 30 ml of isopropyl alcohol (warmed and sonicated) was treated with 1.86 g (7.3 mmoles) of 14 all at once. This was heated under reflux for 2 hours and stirred overnight at room temperature. After this, a small amount of solid (860 mg) was removed and the solution was concentrated to 2.3 g of semi-solid gum. This was chromatographed over 150 g of silica gel 60 using 10% (v/v) CH3OH/CHCl3 saturated with NH3. Three fractions of 150 ml each were taken after an 800-ml forerun. The third fraction provided 1.31 g of a white foam. This was chromatographed again, taking 10-ml fractions. Cuts 17, 18 and 19 provided 80 mg (2.5%) of 15, m.p., 45°-55° C. Mass spectrum, m/e 430 (M+), base peak, m/e 195. Liquid chromatography showed 93.6% purity.
Workup
- temperatureThis was heated
- temperatureunder reflux for 2 hours
- customAfter this, a small amount of solid (860 mg) was removed
- concentrationthe solution was concentrated to 2.3 g of semi-solid gum
- customThis was chromatographed over 150 g of silica gel 60 using 10% (v/v) CH3OH/CHCl3 saturated with NH3
Sources & evidence
- ORD record
- ord-557df545d23b400a942524175615b68c
- Source dataset
- uspto-grants-1989_03
- Patent number
- US04810725
Reaction notes
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