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(Z)-2-ethoxy-3-((2'-(N'-hydroxycarbaMiMidoyl)biphenyl-4-yl)Methyl)-3H-benzo[d]iMidazole-4-carboxylic acid

1397836-49-5
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80841-78-7 Synthesis

80841-78-7
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1449029-77-9
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Yield:1449029-77-9 90 g

Reaction Conditions:

Stage #1: 1-[(2'-(N'-hydroxycarbamimidoyl)[1,1'-biphenyl]-4-yl)methyl]-2-ethoxy-1H-1,3-benzodiazole-7-carboxylic acidwith potassium carbonate in water;N,N-dimethyl-formamide at 80 - 85; for 2 h;
Stage #2: 4-chloromethyl-5-methyl-1,3-dioxol-2-one in water;N,N-dimethyl-formamide at 40 - 45;Temperature;Reagent/catalyst;

Steps:

5.A Preparation of (5-Methyl-2-Oxo-1,3-Dioxol-4-Yl)Methyl 2-Ethoxy-1-{[2'-(N'-Hydroxycarbamimidoyl)Biphenyl-4-Yl]-Methyl}-1H-Benzimidazole-7-Carboxylate (Formula VII)

The 2-ethoxy-1-{[2'-(N'-hydroxycarbamimidoyl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid (100 g) prepared in Example 2A, dimethyl acetamide (450 mL), and potassium carbonate (20.9 g) were heated to 80° C. to 85° C. for 2 hours. The reaction mixture was cooled to 45° C. to 50° C. A solution of 4-(chloromethyl)-5-methyl-1,3-dioxol-2-one (41.44 g) in N,N-dimethylformamide (50 mL) was added to the reaction mixture at 40° C. to 45° C. The reaction mixture was stirred at 45° C. to 55° C. for 6 to 8 hours. The reaction mixture was cooled to 15° C. to 20° C. A solution of sodium bicarbonate (100 g) in water (2000 mL) was added to the reaction mixture. The solid obtained was filtered and washed with water (500 mL) and dried below 50° C. to obtain the title compound. Yield: 90 g

References:

US2015/11774,2015,A1 Location in patent:Paragraph 0070; 0071

76-83-5 Synthesis