4-[4-(Oxiran-2-ylmethoxy)phenyl]-1,2,3-thiadiazole → 4-[4{3-(4-Carbamoylphenoxyethylamino)2-hydroxypropoxy}phenyl]-1,2,3-thiadiazole

HRID 1579054Notes

Reaction equation

HRID 1579054 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[N:13][S:14][CH:15]=2)=[CH:7][CH:6]=1.[C:17]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][NH2:27])=[CH:22][CH:21]=1)(=[O:19])[NH2:18]>C(O)C>[C:17]([C:20]1[CH:29]=[CH:28][C:23]([O:24][CH2:25][CH2:26][NH:27][CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([C:11]3[N:12]=[N:13][S:14][CH:15]=3)=[CH:7][CH:6]=2)=[CH:22][CH:21]=1)(=[O:19])[NH2:18]

Participants

4

Reactant 2

HCID 27371034-[4-(Oxiran-2-ylmethoxy)phenyl]-1,2,3-thiadiazoleHCID 126663984-(2-Aminoethoxy)benzamide

Product 1

HCID 215575394-[4{3-(4-Carbamoylphenoxyethylamino)2-hydroxypropoxy}phenyl]-1,2,3-thiadiazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 234 mg. of 4-[4(2,3-epoxypropoxy)phenyl]-1,2,3-thiadiazole, 180 mg. of 4-carbamoylphenoxyethylamine and 5 ml. of ethanol is stirred at room temperature for 68 hours. The formed precipitate is collected by filtration and recrystallized from methanol thus obtaining the pure 4-[4{3-(4-carbamoylphenoxyethylamino)2-hydroxypropoxy}phenyl]-1,2,3-thiadiazole, m.p. 173°-174° C; λmax 255 nm (ε 32,300); ir 3,345, 1605, 1570 cm-1.

Workup

  1. additionA mixture of 234 mg
  2. filtrationThe formed precipitate is collected by filtration
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-72da262de2984d7b93d0db6f6df77680
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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