ChemicalBook CAS DataBase List BENZOTHIAZOLE-2-CARBOXYLIC ACID

BENZOTHIAZOLE-2-CARBOXYLIC ACID synthesis

14synthesis methods

Product Name:BENZOTHIAZOLE-2-CARBOXYLIC ACID
CAS Number:3622-04-6
Molecular formula:C8H5NO2S
Molecular Weight:179.2

32137-76-1 Synthesis

32137-76-1
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3622-04-6
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$32.00/250mg

Yield: 98%

Reaction Conditions:

with lithium hydroxide in tetrahydrofuran;water at 0 - 10; for 0.5 h;

Steps:

Synthesis of 5-substituted benzo[d]thiazole-2-carboxylic acid (5a):
To the solution of 2 (207mg, 1mmol) in 22 THF (0.5mL) at 10°C was added 107 LiOH·H₂O (42mg, 1mmol, 1equiv) in 99 water (2mL) and stirred magnetically for 30min followed by drop wise addition of dil. 108 HCl (1N) until precipitation occurred. The precipitate was filtered and dried under rotary vacuum evaporation (24 psi) to afford 19 5a in 98% yield, identical (spectral data) with an authentic sample [12]. 4.1.4 19 Benzo[d]thiazole-2-carboxylic acid (5a) (0024) Yield: 175mg, 98% (white solid), mp 104-108°C. IR (KBr) ν: 1708cm^-1. ¹H NMR (400MHz, DMSO-D₆): δ (ppm): 9.43 (s, 1H), 8.19 (d, J=8.52Hz, 1H), 8.12 (d, J=8.44Hz, 1H), 7.57 (dt, J=1.16, 8.2Hz, 1H), 7.51 (dt, J=1.2, 8.08Hz, 1H). ¹³C NMR (100MHz, DMSO-D₆): δ (ppm): 161.43, 159.98, 152.97, 136.26, 127.47, 127.15, 124.68, 122.99; MS (APCI) m/z 180 (M+H) ⁺

References:

Dhameliya, Tejas M.;Tiwari, Rishu;Banerjee, Arkaprabha;Pancholia, Sahaj;Sriram, Dharmarajan;Panda, Dulal;Chakraborti, Asit K. [European Journal of Medicinal Chemistry,2018,vol. 155,p. 364 - 380]