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76350-04-4

5-methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride synthesis

3synthesis methods
N-[3,5-Bis(chlorocarbonyl)-2,4,6-triiodophenyl]amine (100g, 0.17mol) ) was added with 100ml of DMA to dissolve, and methoxyacetyl chloride (27.3g, 0.25mol) was added dropwise at 20°C for about 1 hour. The reaction was kept at 20-30°C for 5-8 hours. Cool the mixture to 5°C, water, potassium carbonate (58.7 g, 0.42 mol), 400 ml of dichloromethane, and 3-amino-1,2-propanediol (17.8 g, 0.2 mol) were added dropwise. After 8 hours, 400 ml of cold water was quickly added to the reaction solution. After crystallization, filtered, washed with a small amount of water, and dried to obtain 5-methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride.
 5-methoxyacetylamino-2,4,6-triiodoisophthalic acid (2,3-dihydroxypropyl)amide chloride
13552-31-3 Synthesis
3-amino-1,2-propanediol, (±)

13552-31-3
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37441-29-5 Synthesis
5-Amino-2,4,6-triiodoisophthaloyl dichloride

37441-29-5
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Yield:76350-04-4 97.4%

Reaction Conditions:

Stage #1: 2-methoxyacetyl chloride;N-[3,5-Bis(chlorocarbonyl)-2,4,6-triiodophenyl]amine in N,N-dimethyl acetamide at 20 - 30;
Stage #2: 3-Amino-1,2-propanediolwith potassium carbonate in dichloromethane;lithium hydroxide monohydrate; for 8 h;Temperature;Solvent;

Steps:

1-16 Example 1

100g (0.17mol) of starting material was added with 100ml of DMA to dissolve, and 27.3g (0.25mol) of methoxyacetyl chloride was added dropwise at 20°C for about 1 hour, and the reaction was kept at 20-30°C for 5-8 hours. Cool to 5°C, add 1 g (0.06 mol) of water, slowly add 58.7 g (0.42 mol) of potassium carbonate, continue to add 400 ml of dichloromethane, and slowly add 17.8 g (0.2 mol) of 3-amino-1,2-propanediol dropwise. After the addition was completed, the reaction was performed for about 8 hours. After the reaction was completed, the reaction solution was quickly added to 400 ml of cold water, crystallized at 0-5 °C for 2 hours, filtered, washed with a small amount of water, and dried to obtain 118.1 g of compound 4, with a yield of 97.4% and a main peak of 99.4%.

References:

CN114436880,2022,A Location in patent:Paragraph 0068-0103

76350-03-3 Synthesis
5-Methoxyacetamido-2,4,6-triiodoisophthaloyl chloride

76350-03-3
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13552-31-3 Synthesis
3-amino-1,2-propanediol, (±)

13552-31-3
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