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

HRID 658109노트

반응식

HRID 658109 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 178493837HCID 178493837, 화합물수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6377b74ea9ee44cfa1ab9030a73c49df
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076367B2

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