5-AMINO-1-BOC-BENZOIMIDAZOLE synthesis

2synthesis methods

Product Name:5-AMINO-1-BOC-BENZOIMIDAZOLE
CAS Number:297756-31-1
Molecular formula:C12H15N3O2
Molecular Weight:233.27

24424-99-5 Synthesis

24424-99-5
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934-22-5 Synthesis

934-22-5
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$21.00/1g

297756-31-1
20 suppliers
$208.00/250mg

297756-32-2 Synthesis

1H-BenziMidazole-1-carboxylicacid,6-aMino-,1,1-diMethylethylester

297756-32-2
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Yield:-

Reaction Conditions:

Stage #1: 5-aminobenzimidazolewith sodium hydride in DMF (N,N-dimethyl-formamide) at 20; for 1 h;
Stage #2: di-tert-butyl dicarbonate in DMF (N,N-dimethyl-formamide) at 0 - 20; for 18 h;

Steps:

3 EXAMPLE 3; 8-[(Z and E)-4-Toluidinomethylidene]-6,8-dihydroimidazo[4,5-e]indol-7(3H)-one

Sodium hydride (7.2 g, 60% in mineral oil, 0.18 mol) was added in portions over 30 min to a stirred solution of 5-aminobenzimidazole (15.0 g, 0.105 mol) in dry DMF (100 mL) and the mixture was stirred at room temperature for 30 min. The reaction mixture was cooled to 0° C. and a solution of di-tert-butyl dicarbonate (24.0 g, 0.110 mol) in dry DMF (25 mL) was added over 10 min. The reaction mixture was stirred at room temperature for 18 h. The solvent was evaporated under reduced pressure and the residue was partitioned between water (200 mL) and diethyl ether (200 mL). The organic phase was separated and the aqueous layer was extracted with diethyl ether. The combined organic extracts were washed with water and brine and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration through a pad of silica gel and the filtrate evaporated to give a mixture of 5- and 6-amino-1-tert-butoxycarbonylbenzimidazole, 21.5 g (84%). H1 NMR (DMSO-d6): δ 8.40 (s, 1H), 8.23 (s, 1H), 7.55 (d, 1H, J=8.8 Hz), 7.34 (d, 1H, J=8.4 Hz), 7.13 (d, 1H, J=1.6 Hz), 6.83 (d, 1H, J=2 Hz), 6.68 (dd, 1H, J=8.8, 1.6 Hz), 6.60 (dd, 1H, J=8.4, 2 Hz), 1.61 (s, 9H), 1.60 (s, 9H).

References:

US6350747,2002,B1 Location in patent:Page column 50-51

tert-butyl 5-nitro-1H-benzo[d]imidazole-
1-carboxylate

1425932-17-7
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1H-Benzimidazole-1-carboxylic acid, 6-nitro-, 1,1-dimethylethyl ester

1442459-46-2
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297756-31-1
20 suppliers
$208.00/250mg

297756-32-2 Synthesis

297756-32-2
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References

5-AMINO-1-BOC-BENZOIMIDAZOLE Related Search:

N-BOC-IMIDAZOLE