Dimethylformamide → 5-chloro-2-[3-(2-phthalimidoacetamidomethyl)-5-propargyloxymethyl-4H-1,2,4-triazol-4-yl]-benzophenone

HRID 25952

反応式

HRID 25952 の反応式
Br.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:17]2[C:21]([CH2:22][O:23][CH2:24][C:25]#[CH:26])=[N:20][N:19]=[C:18]2[CH2:27][NH2:28])=[C:7]([CH:16]=1)[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:9].[C:29]1(=[O:43])[N:33]([CH2:34][C:35](Cl)=[O:36])[C:32](=[O:38])[C:31]2=[CH:39][CH:40]=[CH:41][CH:42]=[C:30]12.CN(C)C=O.C(=O)(O)[O-].[Na+]>C1C=CC=CC=1.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:17]2[C:21]([CH2:22][O:23][CH2:24][C:25]#[CH:26])=[N:20][N:19]=[C:18]2[CH2:27][NH:28][C:35](=[O:36])[CH2:34][N:33]2[C:32](=[O:38])[C:31]3=[CH:39][CH:40]=[CH:41][CH:42]=[C:30]3[C:29]2=[O:43])=[C:7]([CH:16]=1)[C:8]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:9]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 516892Sodium BicarbonateHCID 213257145-chloro-2-(3-aminomethyl-5-propargyloxymethyl-4H-1,2,4-triazol-4-yl)-benzophenone hydrobromide

生成物 1

HCID 213257355-chloro-2-[3-(2-phthalimidoacetamidomethyl)-5-propargyloxymethyl-4H-1,2,4-triazol-4-yl]-benzophenone

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 962Water溶媒

実験手順

A mixture of the above product (817 mg) and 27.5% hydrogen bromide/acetic acid (3 ml) is stirred at room temperature for 1.5 hours. The resultant solution is mixed with dry ether (30 ml) to give a precipitate. The precipitate is washed with dry ether (20 ml) twice to give 5-chloro-2-(3-aminomethyl-5-propargyloxymethyl-4H-1,2,4-triazol-4-yl)-benzophenone hydrobromide. To a suspension of this hydrobromide in dry benzene (20 ml), 2-phthalimidoacetyl chloride (1.6 g) is added at room temperature. The resultant mixture is mixed with dry dimethylformamide (10 ml) and stirred at room temperature for 3 hours. The reaction mixture is poured into saturated aqueous sodium bicarbonate (50 ml)/water (50 ml) and stirred under ice-cooling for 30 minutes. The precipitate is filtered, washed with water and ether in order and dissolved in methylene chloride (about 50 ml). The organic layer is dried over magnesium sulfate and evaporated to remove the solvent. The residue is recrystallized from methylene chloride/ethanol to give 5-chloro-2-[3-(2-phthalimidoacetamidomethyl)-5-propargyloxymethyl-4H-1,2,4-triazol-4-yl]-benzophenone (682 mg) as crystals melting at 245° to 246° C. (decomp.).

後処理

  1. additionis added at room temperature
  2. stirringstirred under ice-
  3. temperaturecooling for 30 minutes
  4. filtrationThe precipitate is filtered
  5. washwashed with water and ether in order
  6. dissolutiondissolved in methylene chloride (about 50 ml)
  7. dry with materialThe organic layer is dried over magnesium sulfate
  8. customevaporated
  9. customto remove the solvent
  10. customThe residue is recrystallized from methylene chloride/ethanol

出典と根拠

ORDレコード
ord-e29611eea3ec4492bf742b0ea11ca39b
出典データセット
uspto-grants-1979_04
特許番号
US04147700

関連ノート

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