5,6-Dichloro-2-benzothiazolamine synthesis
- Product Name:5,6-Dichloro-2-benzothiazolamine
- CAS Number:24072-75-1
- Molecular formula:C7H4Cl2N2S
- Molecular Weight:219.09
333-20-0
95-76-1
24072-75-1
To a solution of acetic acid (160 mL) containing 3,4-dichloroaniline (10 g, 62 mmol) and potassium thiocyanate (48 g, 0.49 mol), a solution of acetic acid (160 mL) with liquid bromine (31 g, 0.19 mol) was slowly added at 0 °C, while stirring was maintained. The reaction temperature was maintained at 0 °C throughout the addition. After addition, the reaction mixture was continued to be stirred at 0 °C for 2 h, and then warmed up to 15 °C for 14 h. The reaction temperature was kept constant at 0 °C for 2 h. The reaction temperature was kept constant at 15 °C for 2 h. Upon completion of the reaction, the reaction solution was diluted with water (100 mL), the pH was adjusted to 7-8 with ammonium hydroxide, and then extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, washed with brine (3 x 300 mL) and subsequently concentrated under reduced pressure. The crude product was purified by preparative HPLC [Apparatus: GX-B; Column: GEMINI 250 × 50 mm, particle size: 10 μm; Mobile phase: 25-50% acetonitrile in water (containing 0.1% TFA, v/v)] to afford the target compound 5,6-dichlorobenzo[d]thiazol-2-amine (2.6 g, 19% yield) as a white solid.LCMS ( ESI): tR = 0.694min, m/z (M+H)+ 219.0. 1H-NMR (CD3OD, 400MHz): δ 7.89 (s, 1H), 7.55 (s, 1H).
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Yield: 19%
Reaction Conditions:
with bromine;acetic acid at 0 - 15; for 16 h;
Steps:
24B Example 24B: 5 ,6-dichlorobenzo [dlthiazol-2-amine (B-24)
j00320j To a mixture of 3,4-dichloroaniline (10 g, 62 mmol) and potassium thiocyanate (48 g, 0.49 mol) in acetic acid (160 mL) at 0 °C was added slowly with constant stirring a solution of liquidbromine (31 g, 0.19 mol) in acetic acid (160 mL). The temperature was maintained at 0 °C throughout the addition. The solution was stirred for 2 hours at 0°C and 14 hours at 15 °C, then diluted with water (100 mL), adjusted to pH 78 with ammonium hydroxide and extracted with ethyl acetate (3 x 50 mL). The combined organic layers were washed with brine (3 x 300 mL) and concentrated in vacuo. The residue was purified by prep-HPLC [Instmment: GX-B; Column: GEMNI 250 x 50 mm, particle size: 10 .im; Mobile phase: 25-50% acetonitrile in H20 (add 0.1% TFA, v/v)j to give compound B- 24 (2.6 g, 19% yield) as a white solid. LCMS (J): tR=0.694 mi (ES) m/z (M+H)219.0. ‘H-NMR (CD3OD, 400 MHz): 7.89 (s, 1H), 7.55 (s, 1H).
References:
FORUM PHARMACEUTICALS, INC.;ACHARYA, Raksha;BURNETT, Duane, A.;BURSAVICH, Matthew, Gregory;COOK, Andrew, Simon;HARRISON, Bryce, Alden;McRINER, Andrew, J. WO2017/69980, 2017, A1 Location in patent:Paragraph 00319; 00320
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95-76-1
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24072-75-1
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19250-09-0
107 suppliers
$21.00/5g
24072-75-1
146 suppliers
$27.00/1g
95-76-1
374 suppliers
$10.00/5g
24072-75-1
146 suppliers
$27.00/1g