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Chloroacetyl chloride → 2-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide

HRID 1809152
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HRID 1809152 반응식
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:17])=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][CH2:2][C:3]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:17])=[C:11]([C:13]([F:16])([F:14])[F:15])[CH:12]=1)=[O:4]
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참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 675744-Chloro-3-(trifluoromethyl)aniline

생성물 1

HCID 23077292-chloro-N-[4-chloro-3-(trifluoromethyl)phenyl]acetamide수율 84.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

To a round bottom flask was added chloroacetyl chloride (2.0 mL, 25.0 mmol, 1.0 eq.) and CH2Cl2 (100 mL). The solution was cooled to 0° C. before a mixture of 5-amino-2-chloro-benzotrifluoride (4.88 g, 25.0 mmol, 1.0 eq.) and triethyl amine (3.56 mL, 27.5 mmol, 1.1 eq.) in CH2Cl2 (5.0 mL) was added dropwise. The reaction was then stirred at 0° C. for 1.5 h before quenching with H2O (50 mL). The organic layer was then separated, washed with brine, and dried with Na2SO4. Concentration via rotary evaporation gave acetamide 21 as a yellow solid (5.72 g, 84.7% yield). 1H-NMR, Varian 400 MHz (DMSO-d6) δ 10.79 (br s, 1H), 8.20 (d, 1H), 7.87 (dd, 1H), 7.75 (d, 1H), 4.36 (s, 2H) ppm.

후처리

  1. additionwas added dropwise
  2. custombefore quenching with H2O (50 mL)
  3. customThe organic layer was then separated
  4. washwashed with brine
  5. dry with materialdried with Na2SO4
  6. concentrationConcentration
  7. customvia rotary evaporation

출처 및 근거

ORD 기록
ord-827dbbb3ee154d9e9d1c7e5a8ea9fd62
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362017B2

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