Isopropylamine → 4-[4(3-Isopropylamino-2hydroxypropoxy)phenyl]-1,2,3-thiadiazole

HRID 1579060Notes

Reaction equation

HRID 1579060 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[O:5]1[CH2:20][CH:6]1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[N:17][S:18][CH:19]=2)=[CH:11][CH:10]=1>C(O)(C)C>[CH:1]([NH:4][CH2:20][CH:6]([OH:5])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[N:17][S:18][CH:19]=2)=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 27371034-[4-(Oxiran-2-ylmethoxy)phenyl]-1,2,3-thiadiazole

Product 1

HCID 215576414-[4(3-Isopropylamino-2hydroxypropoxy)phenyl]-1,2,3-thiadiazole

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 10 g. of isopropylamine, 2 g. of 4-[4(2,3-epoxypropoxy)phenyl]-1,2,3-thiadiazole and 10 ml. of isopropanol is refluxed under stirring for 6 hours. The isopropanol and unreacted isopropylamine are then removed by distillation under vacuo. Crystallization of the residue from methanol-ether produces the pure 4-[4(3-isopropylamino-2hydroxypropoxy)phenyl]-1,2,3-thiadiazole.

Workup

  1. additionA mixture of 10 g
  2. customThe isopropanol and unreacted isopropylamine are then removed by distillation under vacuo
  3. customCrystallization of the residue from methanol-ether

Sources & evidence

ORD record
ord-d2896b4e47a0474fbf521cedeb0243dc
Source dataset
uspto-grants-1976_02
Patent number
US03940407

Reaction notes

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