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Dimethylformamide → 2-Amino-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzonitrile

HRID 1958654
ノート
印刷プレビュー

反応式

HRID 1958654 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[NH2:25].[CH3:26][N:27](C)C=O>C1(C)C=CC=CC=1.[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>[NH2:25][C:3]1[CH:4]=[C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)[CH:6]=[CH:7][C:2]=1[C:26]#[N:27]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 595494992-Bromo-5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenylamine

生成物 1

HCID 595494972-Amino-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzonitrile収率 36%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒
HCID 178418397
HCID 178418397、化合物
触媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-bromo-5-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenylamine (Example I3) (0.840 g, 1.84 mmol) in N,N-dimethylformamide (3 ml) under a nitrogen atmosphere was added zinc(II) cyanide (0.346 g, 2.94 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.255 g, 0.22 mmol). The reaction mixture was stirred at 100° C. for 16 hours. The reaction mixture was diluted with toluene and the phases were separated. The aqueous phase was extracted twice with toluene. The combined organic phases were washed with brine and aqueous ammonium hydroxide (saturated), dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:5) to give 2-amino-4-[5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-benzonitrile (0.480 g, 36% yield). 1H-NMR (CDCl3, 400 MHz): 7.45 (m, 4H), 7.08 (s, 1H), 6.95 (q, 1H), 4.52 (s, 2H), 4.02 (d, 1H), 3.62 (d, 1H).

後処理

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted twice with toluene
  3. washThe combined organic phases were washed with brine and aqueous ammonium hydroxide (saturated)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/cyclohexane 1:5)

出典と根拠

ORDレコード
ord-da58e4eb38fe4bb89b340b82370c0565
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08410145B2

反応ノート

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