Chloride → 5-Amino-2,4,6-triiodo-N~1~,N~3~-dimethylbenzene-1,3-dicarboxamide

HRID 1446857ノート

反応式

HRID 1446857 の反応式
N[C:2]1[C:3]([I:21])=[C:4]([C:9]([I:20])=[C:10]([N:13](CCO)C(=O)C)[C:11]=1[I:12])[C:5]([NH:7][CH3:8])=[O:6].[Cl-].O.C[C:25]([N:27](C)[CH3:28])=[O:26]>>[NH2:13][C:10]1[C:9]([I:20])=[C:4]([C:5]([NH:7][CH3:8])=[O:6])[C:3]([I:21])=[C:2]([C:11]=1[I:12])[C:25]([NH:27][CH3:28])=[O:26]

参加物

5

反応物 4

HCID 312ChlorideHCID 962WaterHCID 31374Dimethylacetamide2 回HCID 12818971HCID 12818971、化合物

生成物 1

HCID 128189555-Amino-2,4,6-triiodo-N~1~,N~3~-dimethylbenzene-1,3-dicarboxamide

実験手順

To a solution of 3-amino-5-[N-(2-hydroxyethyl)acetamido]-2,4,6-triiodo-N-methylbenzamide (II; 50.32 g.; 0.08 mole) dissolved in dimethylacetamide (252 ml.) was added in one portion 2,3,4,5,6-O-pentaacetylgluconyl chloride (101.88 g.; 0.24 mole; prepared by the method of C. E. Braun and C. D. Cook, Org. Syn., 41, 79 (1961)). After being stirred for six days at room temperature, the reaction mixture was poured into a mixture of dimethylacetamide (510 ml.) and water (680 ml.). The mixture was stirred for 2 hours, after which it was extracted with chloroform (3×340 ml.). The combined chloroform extracts were washed with 5% aqueous bicarbonate (2×340 ml.) and water (340 ml.), dried over sodium sulfate and evaporated under reduced pressure to give III as an oil, 132.75 g. (>100% due to the presence of dimethylacetamide as shown by the nuclear magnetic resonance spectrum). The product was homogeneous by thin-layer chromatography (ethyl acetate-acetic acid, 98:2), and the nuclear magnetic resonance spectrum was consistent with the assigned structure. The product was hydrolyzed without further purification.

後処理

  1. customprepared by the method of C
  2. stirringThe mixture was stirred for 2 hours
  3. extractionafter which it was extracted with chloroform (3×340 ml.)
  4. washThe combined chloroform extracts were washed with 5% aqueous bicarbonate (2×340 ml.) and water (340 ml.)
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-8074733e025545fda7624e727f431eec
出典データセット
uspto-grants-1982_02
特許番号
US04314055

反応ノート

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