Potassium Carbonate → 4-(4,5-dichloro-2-(4-chloro-2-methoxyphenoxy)benzamido)benzoic Acid

HRID 515098

반응식

HRID 515098 반응식
[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][CH:10]=2)=[O:7])=[C:4](F)[CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([O:31][CH3:32])[CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CO.CN1CCCC1=O>[Cl:1][C:2]1[C:20]([Cl:21])=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[O:7])=[C:4]([O:30][C:27]2[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][C:26]=2[O:31][CH3:32])[CH:3]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 14798Sodium Hydroxide2회HCID 280504-ChloroguaiacolHCID 90314713Methyl 4-[(4,5-dichloro-2-fluoro-benzoyl)amino]benzoate

생성물 1

HCID 778449964-(4,5-dichloro-2-(4-chloro-2-methoxyphenoxy)benzamido)benzoic Acid수율 25.2%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

A mixture of methyl 4-[(4,5-dichloro-2-fluoro-benzoyl)amino]benzoate (34.21 mg, 0.1 mmol), 4-chloro-2-methoxyphenol (12.16 μl, 0.1 mmol), potassium carbonate 13.82 mg, 0.1 mmol) and N-methylpyrrolidinone (1 mL) were heated at 80° C. for 2.5 hours. Methanol (100 μL) and sodium hydroxide (3M, 100 μL, 0.3 mmol) were added and the reaction was stirred at 50° C. for 2 hours. An additional 100 μL of MeOH and 100 μL of 3M NaOH were added and the reactions were heated for another hour. The reaction mixture was filtered and purified by reverse phase preparative chromatography utilizing a gradient of 10-99% acetonitrile in water containing HCl as a modifier to yield 4-(4,5-dichloro-2-(4-chloro-2-methoxyphenoxy)benzamido)benzoic acid (18) (11.78 mg, 25%). ESI-MS m/z calc. 464.99, found 466.3 (M+1)+; Retention time: 2.20 minutes (3 minutes run).

후처리

  1. temperaturethe reactions were heated for another hour
  2. filtrationThe reaction mixture was filtered
  3. custompurified by reverse phase preparative chromatography
  4. additioncontaining HCl as a modifier

출처 및 근거

ORD 기록
ord-90107f4e243b4436b44164a7c88a4546
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108903B2

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