Triethylamine → methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate

HRID 2116686노트

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HRID 2116686 반응식
C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Br[C:24]1[CH:30]=[C:29]([CH3:31])[C:27]([NH2:28])=[C:26]([Cl:32])[CH:25]=1.[C:33]([NH:36][C:37](=[CH2:42])[C:38]([O:40][CH3:41])=[O:39])(=[O:35])[CH3:34].C(N(CC)CC)C>C(#N)C>[C:33]([NH:36]/[C:37](=[CH:42]/[C:24]1[CH:30]=[C:29]([CH3:31])[C:27]([NH2:28])=[C:26]([Cl:32])[CH:25]=1)/[C:38]([O:40][CH3:41])=[O:39])(=[O:35])[CH3:34]

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 27696264-Bromo-2-chloro-6-methylaniline

생성물 1

HCID 69363659methyl (E)-2-acetylamino-3-(4-amino-3-chloro-5-methyl-phenyl)-acrylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

Under protective nitrogen gas 2.02 g (9.0 mmol) palladium(II)acetate and 2.82 g (9.0 mmol) tri-o-tolylphosphine were added to a mixture of 25.0 g (113 mmol) 4-bromo-2-chloro-6-methyl-aniline, 19.9 g (136 mmol) methyl 2-acetamidoacrylate, 350 ml triethylamine and 150 ml acetonitrile at ambient temperature. The reaction mixture was stirred for 18 hours at 80° C., evaporated down under reduced pressure, the residue was combined with 600 ml dichloromethane and water and filtered off from the insoluble precipitate. The organic phase was dried over sodium sulphate, evaporated down under reduced pressure and then combined with 200 ml of ethyl acetate/cyclohexane (3/1). The insoluble fraction was suction filtered and the mother liquor was purified by column chromatography through silica gel. The corresponding fractions were evaporated down under reduced pressure and combined with the insolublen fraction suction filtered previously.

후처리

  1. customevaporated down under reduced pressure
  2. filtrationfiltered off from the insoluble precipitate
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. customevaporated down under reduced pressure
  5. filtrationfiltered
  6. customthe mother liquor was purified by column chromatography through silica gel
  7. customThe corresponding fractions were evaporated down under reduced pressure
  8. filtrationfiltered previously

출처 및 근거

ORD 기록
ord-19903001339744e3bed1780a61a27394
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07439237B2

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