Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 178493837、化合物

HRID 2233783ノート

反応式

HRID 2233783 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)=[O:24])[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]([OH:22])[CH2:20][OH:21])[CH:14]=1)=[O:12].[C:32]([O-])([O-])([O:34][CH3:35])[CH3:33].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]1=[C:10]([C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([CH:19]2[CH2:20][O:21][C:32]([O:34][CH3:35])([CH3:33])[O:22]2)[CH:14]=1)=[O:12])[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)=[O:24]

参加物

5

反応物 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 536300401-Methoxyethane-1,1-diolateHCID 178520867HCID 178520867、化合物

生成物 1

HCID 178493837HCID 178493837、化合物収率 68%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A 6 ml portion of THF solution containing 0.21 g of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-[3-(1,2-dihydroxyethyl)phenyl]-3-(3-fluorophenyl)propane-1,3-dione and 0.3 g of methyl orthoacetate was mixed with 63 mg of pyridinium p-toluenesulfonate and then stirred at room temperature for about 30 minutes. After evaporation of the solvent, the residue was mixed with an appropriate amount of sodium bicarbonate aqueous solution, extracted several times with ethyl acetate, dried with anhydrous magnesium sulfate and concentrated. The thus formed residue was purified by a silica gel column chromatography to obtain 162 mg (68%) of 2-(1,3-dihydro-2H-benzimidazol-2-ylidene)-1-(3-fluorophenyl)-3-[3-(2-methoxy-2-methyl-1,3-dioxolan-4-yl)phenyl]propane-1,3-dione (Example 3-1) as a pale yellow foam from an ethyl acetate-hexane (1:2) eluate.

後処理

  1. customAfter evaporation of the solvent
  2. additionthe residue was mixed with an appropriate amount of sodium bicarbonate aqueous solution
  3. extractionextracted several times with ethyl acetate
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe thus formed residue was purified by a silica gel column chromatography

出典と根拠

ORDレコード
ord-231ea32e2b0842759dd126196d747b53
出典データセット
uspto-grants-2010_05
特許番号
US07709519B2

反応ノート

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