2-AMINO-4-BROMOBENZENETHIOL synthesis

6synthesis methods

Product Name:2-AMINO-4-BROMOBENZENETHIOL
CAS Number:93933-49-4
Molecular formula:C6H6BrNS
Molecular Weight:204.09

63837-11-6 Synthesis

63837-11-6
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Yield: 96%

Reaction Conditions:

with water;sodium hydroxide in ethylene glycol at 140; for 4 h;

Steps:

23.1 Step1: 2 -Amino-4-bromobenzenethiol
To a stirring solution of 5-bromo-2-methylbenzo[djthiazole (5 g, 22.02 mmol) in ethylene glycol (50 mL) was added 8N sodium hydroxide solution (50 mL) and the resulting reaction mixture was stirred at 140 °C for 4 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was concentrated under reduced pressure to get a crude residue, which was purified by triturating it with pentane/ether to afford the title compound as a yellow solid (4.3 g, 96% yield). ‘H NMR (400 MHz, DMSO-d6) = 7.09 (d, J=8.33 Hz, 1H), 6.87 (d, J=1.75 Hz, 1H), 6.62 (dd, J=1.75, 8.33 Hz, 1H), 5.16 (br. s, 3H). LCMS: [M+Hj = 203.83; R = 3.10 mm.

References:

SYROS PHARMACEUTICALS, INC.;ROBERTS, Christopher;ZHANG, Yi;BEAUMIER, Francis;LEPISSIER, Luce;MARINEAU, Jason, J.;RAHL, Peter, B.;SPROTT, Kevin;CIBLAT, Stephane;SOW, Boubacar;LAROUCHE-GAUTHIER, Robin;BERSTLER, Lauren WO2016/197078, 2016, A1 Location in patent:Paragraph 395; 396-397; 565; 566-567; 935-936; 950-951; 1010