Water → 1-[4-(3-Carbamoyl-4-hydroxyphenoxy)butylamino]-3-(2-cyanophenoxy)propan-2-ol
Reaction equation
[O:1]1[CH2:13][CH:2]1[CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8].[NH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:28]=[C:24]([C:25]([NH2:27])=[O:26])[C:23]([OH:29])=[CH:22][CH:21]=1.O>CS(C)=O>[C:25]([C:24]1[CH:28]=[C:20]([CH:21]=[CH:22][C:23]=1[OH:29])[O:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][CH2:13][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[C:7]#[N:8])(=[O:26])[NH2:27]Participants
5
Procedure
7.3 g of 2-(2,3-epoxypropoxy)benzonitrile are added to a solution of 6.7 g of 5-(4-aminobutoxy)salicylamide in 60 ml of dimethyl sulphoxide and the mixture is stirred for 1 hour in a bath at 90°. The reaction mixture is poured into 300 ml of water and extracted twice with 200 ml of ethyl acetate each time. Working up analogously to Example 23 yields crude 1-[4-(3-carbamoyl-4-hydroxyphenoxy)butylamino]-3-(2-cyanophenoxy)propan-2-ol as a viscous oil, the IR- and 1H-NMR-spectra of which are in concordance with the assumed structure and the Rf-value of which is 0,51 according to thin-layer-chromatography on silicagel using a mixture of ethylacetate-ethanol-conc. ammonia 24:12:4 as the eluent.
Workup
- extractionextracted twice with 200 ml of ethyl acetate each time
Sources & evidence
- ORD record
- ord-3932fd720e6245d682e4d11e1b44d383
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04636511
Reaction notes
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