Hydrogen Peroxide → HCID 178520014, compound

HRID 1754259Notes

Reaction equation

HRID 1754259 reaction equation
[C:1]1([C:7]2[CH:22]=[CH:21][C:10]3[N:11]=[C:12]([CH2:14][C:15]4[O:19][C:18]([OH:20])=[N:17][N:16]=4)[S:13][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.BrC1C=CC2N=C(CC3[O:36]C(O)=NN=3)SC=2C=1.OO>C(O)(=O)C.O>[OH:20][C:18]1[O:19][C:15]([C:14]([C:12]2[S:13][C:9]3[CH:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:22]=[CH:21][C:10]=3[N:11]=2)=[O:36])=[N:16][N:17]=1

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 1785189165-((6-Bromobenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-olHCID 178518917HCID 178518917, compound

Product 1

HCID 178520014HCID 178520014, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of 5-((6-phenylbenzo[d]thiazol-2-yl)methyl)-1,3,4-oxadiazol-2-ol (25 mg, 0.081 mmol) in acetic acid (1 mL) (prepared according to a similar procedure described for Compound 51a) was added 30% hydrogen peroxide in water (0.17 mL, 1.6 mmol) and the reaction mixture heated at 50° C. for 16 h. The reaction mixture was allowed to cool to rt then diluted with water and filtered. The solid was washed with water and rinsed with ether, then dried under vacuum to afford Compound 88a (21 mg, 80% yield) as a yellow solid. LCMS=0.96 min using analytical method (M), 324.1 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 8.64 (d, J=1.5 Hz, 1H), 8.40 (d, J=8.5 Hz, 1H), 8.02 (dd, J=8.5, 1.8 Hz, 1H), 7.89-7.79 (m, 2H), 7.63-7.50 (m, 2H), 7.50-7.41 (m, 1H), 5.76 (s, 1H).

Workup

  1. customprepared
  2. temperatureto cool to rt
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. washrinsed with ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-f6f65134d87a4d2eaabc316714e55f51
Source dataset
uspto-grants-2015_10
Patent number
US09169240B2

Reaction notes

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