Reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([CH2:11][C:12](O)=[O:13])[C:9](=[S:15])[NH:8][N:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:13][CH2:12][CH2:11][N:10]1[C:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[N:7][NH:8][C:9]1=[S:15]Participants
Procedure
All of the crude [3-(2-thienyl)-5-thioxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]acetic acid from the previous step was dissolved in THF (20 ml). This solution was added dropwise at 0° C. to a slurry of LAH (2 g) in THF (80 ml) while stirring before allowed to come to r.t. for 2 h. The r.m. was then quenched with sat. Na2SO4 (aq.) at 0° C. and the pH adjusted to 3-4 before filtration through celite. The THF was removed from the filtrate by concentration and the product extracted with EA from the remaining aq. mixture. The EA-phase was then washed with brine and dried over MgSO4 before concentration to dryness to yield a crude material that was recrystallized from MeOH to provide 485 mg of the title compound. 1H NMR (DMSO-d6): 13.94 (br.s, 1H), 7.86 (d, 1H), 7.81 (d, 1H), 7.24 (dd, 1H), 5.09 (t, 1H), 4.16 (t, 2H), 3.76 (q, 2H)
Workup
- customwas then quenched with sat. Na2SO4 (aq.) at 0° C.
- filtrationthe pH adjusted to 3-4 before filtration through celite
- customThe THF was removed from the filtrate by concentration
- extractionthe product extracted with EA from the remaining aq. mixture
- washThe EA-phase was then washed with brine
- dry with materialdried over MgSO4 before concentration to dryness
- customto yield a crude material that
- customwas recrystallized from MeOH
Sources & evidence
- ORD record
- ord-c5634c107a28449f99d20628a3f79c4c
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576077B2
Linked notes
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