Isopropylamine → HCID 20467337, compound

HRID 1903400Notes

Reaction equation

HRID 1903400 reaction equation
[O:1]1[CH2:14][CH:2]1[CH2:3][O:4][C:5]1[C:13]2[C:9](=[N:10][S:11][N:12]=2)[CH:8]=[CH:7][CH:6]=1.[CH:15]([NH2:18])([CH3:17])[CH3:16]>O1CCOCC1>[CH:15]([NH:18][CH2:14][CH:2]([OH:1])[CH2:3][O:4][C:5]1[C:13]2[C:9](=[N:10][S:11][N:12]=2)[CH:8]=[CH:7][CH:6]=1)([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 13064030HCID 13064030, compound

Product 1

HCID 20467337HCID 20467337, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.2 g (25 mM) 4-(2,3-epoxypropyloxy)-2,1,3-benzthiadiazole in 60 ml. dioxan were heated under reflux for 4 hours with 30 ml. isopropylamine. The reaction mixture was then evaporated and the residue was chromatographed on a silica gel column (silica gel particle size 0.063-0.200 mm., elution agent methanol with a small addition of glacial acetic acid). The residue obtained after evaporation of the eluted fractions was recrystallized from diisopropyl ether. There were obtained 4.1 g (62% of theory) 4-(3-isopropylamino-2-hydroxy-propyloxy)-2,1,3-benzthiadiazole, which had a melting point of 100°-102° C.

Workup

  1. temperatureunder reflux for 4 hours with 30 ml
  2. customThe reaction mixture was then evaporated
  3. customthe residue was chromatographed on a silica gel column (silica gel particle size 0.063-0.200 mm
  4. wash, elution agent methanol
  5. additionwith a small addition of glacial acetic acid)
  6. customThe residue obtained
  7. customafter evaporation of the eluted fractions
  8. customwas recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-7d18df853250451085bc3ce181663c11
Source dataset
uspto-grants-1984_03
Patent number
US04436742

Reaction notes

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