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].NCCCC[C:19]1[CH:27]=[C:23]([C:24]([NH2:26])=[O:25])[C:22]([OH:28])=[CH:21][CH:20]=1.[OH2:29]>CS(C)=O>[C:24]([C:23]1[CH:27]=[C:19]([CH:20]=[CH:21][C:22]=1[OH:28])[O:29][CH2:12][CH2:5][CH2:6][CH2:7][NH:8][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:25])[NH2:26]Participants
5
Procedure
7.3 g of 2-(2,3-epoxypropoxy)benzonitrile are added to a solution of 6.7 g of 5-(4-aminobutyl)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-d6c6a7798fa54baab3dca6d9fadb6042
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04727067
Reaction notes
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