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N,N-Dimethylaniline → N-(2,4-dichloro-6-methylpyridin-3-yl)-2-bromoacetamide

HRID 348581
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HRID 348581 반응식
[NH2:1][C:2]1[C:3]([Cl:10])=[N:4][C:5]([CH3:9])=[CH:6][C:7]=1[Cl:8].CN(C)C1C=CC=CC=1.[Br:20][CH2:21][C:22](Br)=[O:23].O>C(Cl)(Cl)Cl>[Cl:10][C:3]1[C:2]([NH:1][C:22](=[O:23])[CH2:21][Br:20])=[C:7]([Cl:8])[CH:6]=[C:5]([CH3:9])[N:4]=1
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참가 물질

6

반응물 4

HCID 949N,N-DimethylanilineHCID 962WaterHCID 61147Bromoacetyl bromide2회HCID 106311302,4-Dichloro-6-methylpyridin-3-amine

생성물 1

HCID 10266671N-(2,4-dichloro-6-methylpyridin-3-yl)-2-bromoacetamide수율 73%

시약·촉매·용매 1

HCID 6212Chloroform
용매
3회

실험 절차

3-Amino-2,4-dichloro-6-methylpyridine (48.0 g, 271.1 mmol) was dissolved in chloroform (384 mL), and N,N-dimethylaniline (39.4 g, 325.1 mmol) was added to the solution. A solution of bromoacetyl bromide (65.7 g, 325.5 mmol) in chloroform (96 mL) was added dropwise to the mixture under stirring and under cooling with ice. The resultant mixture was stirred for 1 hour at the same temperature and for 1 hour at room temperature. Subsequently, under cooling with ice, a solution of bromoacetyl bromide (27.4 g, 135.7 mmol) in chloroform (48 mL) was further added to the resultant mixture, followed by stirring for 1 hour at room temperature. Water (288 mL) was added to the reaction mixture, and the resultant mixture was stirred for 12 hours at room temperature. The reaction mixture was stirred for 2 hours under cooling with ice, and the precipitated crystals were collected through filtration. The crystals were washed with cold ethanol (96 mL) and dried at 50° C. by use of a blower, to thereby yield 58.81 g of N-(2,4-dichloro-6-methylpyridin-3-yl)-2-bromoacetamide (yield: 73%) as colorless crystals.

후처리

  1. temperatureunder cooling with ice
  2. temperatureSubsequently, under cooling with ice
  3. stirringby stirring for 1 hour at room temperature
  4. stirringThe reaction mixture was stirred for 2 hours
  5. temperatureunder cooling with ice
  6. filtrationthe precipitated crystals were collected through filtration
  7. washThe crystals were washed with cold ethanol (96 mL)
  8. customdried at 50° C. by use of a blower

출처 및 근거

ORD 기록
ord-4a5bdd1550fa4be9af8f4e21df34b6b4
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07176306B2

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