CarbaMic acid, N-(3,4-diaMinophenyl)-, 1,1-diMethylethyl ester synthesis
- Product Name:CarbaMic acid, N-(3,4-diaMinophenyl)-, 1,1-diMethylethyl ester
- CAS Number:937372-03-7
- Molecular formula:C11H17N3O2
- Molecular Weight:223.27
219492-81-6
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937372-03-7
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Yield:-
Reaction Conditions:
with hydrogen;palladium 10% on activated carbon in methanol at 20; for 1 h;
Steps:
1
A solution OF 2-NITRO-BENZENE-1, 4-diamine (1-1,1. 01 g, 6.53 mol) in tert-butanol (20 mL) was treated with di-tert-butyl dicarbonate (1.42 g, 6.53 mol) and heated at 40C. After lh stirring at the same temperature, the reaction mixture was cooled to the ambient temperature and concentrated in vacuo. The resulting crude mixture was dissolved in ethyl acetate, treated with active carbon, and filtered though a pad of Celite (3 g). The filtrate solution was concentrated in vacuo to afford the desired product as a deep orange powder. The intermediate (1-2) was dissolved in methanol (20 mL) and mixed with palladium on carbon (10%, 50 mg). Hydrogen gas was bubbled into the reaction mixture at the ambient temperature for LH. Any insoluble material was removed by filtration and the filtrate solution was concentrated in vacuo. The resulting crude product was triturated with ethyl acetate (10 mL) and hexanes (2 mL) to give (4- Amino-3-nitro-phenyl) -carbamic acid tert-butyl ester (1-3) as a pale gray solid. The product was stored at-15 OC in a brown bottle ; 1H NMR (500 MHz, DMSO-d6) 8 8.82 (s, 1 H), 6.84 (s, 1 H), 6.56 (d, 1 H, J = 8.5 Hz), 6.49 (d, 1 H, J = 8.0 Hz), 5.71 (bs, 4 H).
References:
WO2004/41277,2004,A1 Location in patent:Page/Page column 66
24424-99-5
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937372-03-7
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5307-14-2
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937372-03-7
16 suppliers
$500.06/5MG