Water → 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(4-methyl-5-methylthio-4H-1,2,4-triazol-3-yl)-phenoxy]-2-propanol

HRID 638064Notes

Reaction equation

HRID 638064 reaction equation
[O:1]1[CH2:19][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[C:14]([S:17][CH3:18])=[N:13][N:12]=2)=[CH:7][CH:6]=1.[NH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:32]=[C:28]([C:29]([NH2:31])=[O:30])[C:27]([OH:33])=[CH:26][CH:25]=1.O>CS(C)=O>[C:29]([C:28]1[CH:32]=[C:24]([CH:25]=[CH:26][C:27]=1[OH:33])[O:23][CH2:22][CH2:21][NH:20][CH2:19][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:15]([CH3:16])[C:14]([S:17][CH3:18])=[N:13][N:12]=2)=[CH:7][CH:6]=1)(=[O:30])[NH2:31]

Participants

5

Reactant 3

HCID 962WaterHCID 202550733-[4-(2,3-epoxypropoxy)-phenyl]-4-methyl-5-methylthio-4H-1,2,4-triazoleHCID 230496945-(2-Aminoethoxy)-2-hydroxybenzamide

Product 1

HCID 202550801-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(4-methyl-5-methylthio-4H-1,2,4-triazol-3-yl)-phenoxy]-2-propanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Analogously to Example 12, 19.5 g of 3-[4-(2,3-epoxypropoxy)-phenyl]-4-methyl-5-methylthio-4H-1,2,4-triazole are reacted with 11.0 g of 5-(2-aminoethoxy)-salicylamide in 70 ml of dimethyl sulphoxide. The resin-like crude product that is obtained on mixing with water is extracted by boiling with dioxan, the dioxan solution is concentrated by evaporation and the residue is recrystallised from methanol. 1-[2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(4-methyl-5-methylthio-4H-1,2,4-triazol-3-yl)-phenoxy]-2-propanol having a melting point of 123°-125° is obtained.

Workup

  1. customThe resin-like crude product that is obtained
  2. extractionis extracted
  3. concentrationthe dioxan solution is concentrated by evaporation
  4. customthe residue is recrystallised from methanol

Sources & evidence

ORD record
ord-d39aa8b413344994b776d96ec1cb62d3
Source dataset
uspto-grants-1985_12
Patent number
US04559354

Reaction notes

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