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Oxalyl chloride → 5-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide

HRID 558387
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HRID 558387 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([OH:10])=O)#[N:2].C(Cl)(=O)C(Cl)=O.[F:20][C:21]([F:32])([F:31])[O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[C:25]([Cl:30])[CH:24]=1.C(N(CC)C(C)C)(C)C>ClCCl.O1CCCC1.CN(C)C=O>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7]([CH:11]=1)[C:8]([NH:27][C:26]1[CH:28]=[CH:29][C:23]([O:22][C:21]([F:20])([F:31])[F:32])=[CH:24][C:25]=1[Cl:30])=[O:10])#[N:2]
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참가 물질

8

반응물 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27340842-Chloro-4-(trifluoromethoxy)anilineHCID 219425685-Cyano-2-methoxybenzoic acid

생성물 1

HCID 231415205-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide수율 90%

시약·촉매·용매 3

HCID 6228
Dimethylformamide
용매
HCID 6344Dichloromethane용매
HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

5-Cyano-2-methoxybenzoic acid (0.73 g) obtained in step A, and 16 μL of N,N-dimethylformamide were dissolved in 18 mL of dichloromethane, and the solution was cooled to 0° C. To this solution, 0.54 mL of oxalyl chloride was added little by little, and the mixture was stirred for 2.7 hours at room temperature. The reaction mixture was distilled under reduced pressure, and dried to obtain a light yellow solid. This solid was added, with the use of 10 mL of tetrahydrofuran, to a solution of 0.95 g of 4-trifluoromethoxy-2-chloroaniline and 2.1 mL of N,N-diisopropylethylamine dissolved in 20 mL of tetrahydrofuran. The mixture was stirred overnight at room temperature, and then tetrahydrofuran was distilled off under reduced pressure. The resulting solid was purified by silica gel column chromatography using methylene chloride as an elution solvent, thereby obtaining 1.37 g (90%) of 5-cyano-N-(4-trifluoromethoxy-2-chlorophenyl)-2-methoxybenzamide.

후처리

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customdried
  3. customto obtain a light yellow solid
  4. stirringThe mixture was stirred overnight at room temperature
  5. distillationtetrahydrofuran was distilled off under reduced pressure
  6. customThe resulting solid was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-efb8ac4fa6d949e7a794632ee3ab3f67
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08063046B2

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