Methyl Isobutyl Ketone → 5-[[2-hydroxy-3-[3-(1-pieridinylmethyl)phenoxy]propyl]amino]-1-methyl-1H-1,2,4-triazole-3-methanol

HRID 1589541Notes

Reaction equation

HRID 1589541 reaction equation
[NH2:1][CH2:2][CH:3]([OH:16])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:7]=1.C([O:20][CH2:21][C:22]([N:24]=[C:25]([N:28]([CH3:37])[N:29]=CC1C=CC=CC=1)SC)=O)(=O)C.[CH2:38]([C:42](C)=O)[CH:39](C)C>>[OH:16][CH:3]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][N:13]2[CH2:14][CH2:42][CH2:38][CH2:39][CH2:15]2)[CH:7]=1)[CH2:2][NH:1][C:25]1[N:28]([CH3:37])[N:29]=[C:22]([CH2:21][OH:20])[N:24]=1

Participants

4

Reactant 3

HCID 7909Methyl Isobutyl KetoneHCID 132801341-Amino-3-{3-[(dimethylamino)methyl]phenoxy}propan-2-olHCID 53735339Methyl N-[2-(acetyloxy)acetyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate

Product 1

HCID 202459995-[[2-hydroxy-3-[3-(1-pieridinylmethyl)phenoxy]propyl]amino]-1-methyl-1H-1,2,4-triazole-3-methanol

Procedure

Similarly prepared by this procedure from 1-amino-3-[3-(dimethylaminomethyl)phenoxy]-2-propanol (1.5 g) and compound B (2.25 g) except that the methyl isobutyl ketone extract was evaporated to give a solid which was washed with diethyl ether and then recrystallised from methyl acetate was 5-[[3-[3-(dimethylaminomethyl)phenoxy]-2-hydroxy-propyl]amino]-1-methyl-1H-1,2,4-triazole-3-methanol (250 mg) m.p. 104°-109°.

Workup

  1. extractionextract
  2. customwas evaporated
  3. customto give a solid which
  4. washwas washed with diethyl ether
  5. customrecrystallised from methyl acetate

Sources & evidence

ORD record
ord-20795e82c31041db8158a8cef02993c5
Source dataset
uspto-grants-1986_02
Patent number
US04571394

Reaction notes

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