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Hydrochloric Acid → Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamate

HRID 495632
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HRID 495632 반응식
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[C:5]([N:12]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[C:13](=[O:17])[O:14][CH2:15][CH3:16])=[C:4]([N+:26]([O-:28])=[O:27])[CH:3]=1.Cl.[CH3:30][N:31](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:12]([C:5]1[C:6]([C:8]([F:11])([F:10])[F:9])=[CH:7][C:2]([C:30]#[N:31])=[CH:3][C:4]=1[N+:26]([O-:28])=[O:27])[C:13](=[O:17])[O:14][CH2:15][CH3:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 22327381Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate

생성물 1

HCID 69744412Ethyl 2-chlorobenzyl[4-cyano-2-nitro-6-(trifluoromethyl)phenyl]carbamate수율 59%

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매
HCID 178418397
HCID 178418397, 화합물
촉매

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온도
60 °C

실험 절차

Ethyl 4-bromo-2-nitro-6-(trifluoromethyl)phenyl(2-chlorobenzyl)carbamate (620.3 mg) was dissolved in N,N-dimethylformamide (30 ml), and to the solution were added zinc cyanide (302.4 mg) and tetrakis(triphenylphosphine)palladium(0) (1.116 g). The mixture was heated at 60° C. and stirred for 7 hours. After allowing to cool, to the reaction mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=3:1) to give the title compound (322.6 mg, 59%).

후처리

  1. temperatureto cool, to the reaction mixture
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by silica gel column (100 g, hexane:ethyl acetate=3:1)

출처 및 근거

ORD 기록
ord-d4498674f1fa409bba71912b1bf7b4ed
출처 데이터셋
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06939887B2

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