Hydrochloric Acid → 2-(1,3-Benzothiazol-2-yl)-6-methoxyphenol

HRID 589262Notes

Reaction equation

HRID 589262 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].O=[CH:10][C:11]1[CH:19]=[CH:18][CH:17]=[C:14]([O:15][CH3:16])[C:12]=1[OH:13].OO.Cl>CCO>[OH:13][C:12]1[C:14]([O:15][CH3:16])=[CH:17][CH:18]=[CH:19][C:11]=1[C:10]1[S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 87132-AminothiophenolHCID 8991o-Vanillin

Product 1

HCID 957542-(1,3-Benzothiazol-2-yl)-6-methoxyphenolYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

HMBT was synthesized according to a previous reported method with minor modifications (Guo et al., Chin. Chem. Lett. 2009, 20, 1408-1410. A solution of 2-aminothiophenol (0.3 mL, 4.2 mmol) and o-vanillin (0.48 g, 3.15 mmol) in EtOH (10 mL), aq H2O2 (30%, 18.9 mmol) and aq HCl (37%, 9.45 mmol) was stirred at room temperature for 90 min. The solution was quenched by 10 mL H2O. The precipitate was filtered, dried under vacuum and recrystallized from EtOH to afford the desired product as a light yellow solid (0.64 g, 79% yield). 1H NMR (CDCl3, 400 MHz), δ (ppm): 12.75 (s, 1H), 8.01 (d, 1H, J=7.6 Hz), 7.91 (d, 1H, J=7.2 Hz), 7.51 (t, 1H, J=6.8 Hz), 7.42 (t, 1H, J=7.2 Hz), 7.33 (dd, 1H, J1=1.2 Hz, J2=8.0 Hz), 6.99 (dd, 1H, J1=1.2 Hz, J2=8.0 Hz), 6.91 (t, 1H, J=8.0 Hz), 3.96 (s, 1H). 13C NMR (CDCl3, 100 MHz), δ 169,74, 151.86, 149.13, 148.29, 136.47, 132.70, 126.80, 125.66, 122.36, 121.59, 120.11, 119.23, 116.86, 114.21, 56.36. ESI-FTMS m/z=258.0587 [M+H]+, calc. 258.0589 for C14H12NO2S.

Workup

  1. customHMBT was synthesized
  2. customThe solution was quenched by 10 mL H2O
  3. filtrationThe precipitate was filtered
  4. customdried under vacuum
  5. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-83dc0b0b05ea419894cbf770199e389d
Source dataset
uspto-grants-2016_01
Patent number
US09229007B2

Reaction notes

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