Hydrochloric Acid → 4-Cyano-7-fluoro-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide

HRID 17372

반응식

HRID 17372 반응식
[CH3:1][N:2](C)[CH3:3].Cl.CNC.[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20](OCC)=[O:21])[O:19][C:15]=2[C:14]([F:25])=[C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]=1[CH3:32])#[N:10].Cl>ClCCl>[C:9]([C:11]1[C:16]2[N:17]=[C:18]([C:20]([N:2]([CH3:3])[CH3:1])=[O:21])[O:19][C:15]=2[C:14]([F:25])=[C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:12]=1[CH3:32])#[N:10]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 1146TrimethylamineHCID 10473Dimethylamine, hydrochlorideHCID 51041426Ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate

생성물 1

HCID 510423354-Cyano-7-fluoro-N,N,5-trimethyl-6-phenyl-1,3-benzoxazole-2-carboxamide수율 67%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Under nitrogen atmosphere, trimethylamine (1.03 M n-hexane solution, 2.25 ml, 2.31 mmol) was dropwise added at room temperature to a dichloromethane (3 ml) solution of dimethylamine hydrochloride (189 mg, 2.31 mmol), followed by stilling for 25 minutes. Subsequently, a dichloromethane (2 ml) solution of ethyl 4-cyano-7-fluoro-5-methyl-6-phenyl-1,3-benzoxazole-2-carboxylate (I-111) (250 mg, 771 μmol) was dropwise added, followed by stirring for 17 hours. After the reaction, aqueous 1N hydrochloric acid solution was added to the reaction liquid with cooling with ice, followed by stirring at room temperature, and the reaction liquid was extracted with chloroform. Next, the obtained organic layers were combined, dried oil anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was suspended and washed in diethyl ether to obtain the entitled compound (167 mg, 67%) as a white solid.

후처리

  1. additionwas added to the reaction liquid
  2. temperaturewith cooling with ice
  3. stirringby stirring at room temperature
  4. customthe reaction liquid
  5. extractionwas extracted with chloroform
  6. dry with materialdried oil anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. washwashed in diethyl ether

출처 및 근거

ORD 기록
ord-5773ebbef3794497a5c28665ce409701
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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