Phosphorus pentachloride → N-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonoyl chloride

HRID 59224

反応式

HRID 59224 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]/[N:9]=[CH:10]/[C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:20]>C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][N:9]=[C:10]([Cl:20])[C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 24819Phosphorus pentachlorideHCID 900336584-bromo-N-[(E)-(2-chloro-6-fluorophenyl)methylideneamino]aniline

生成物 1

HCID 131733232N-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonoyl chloride収率 23%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

To a solution of (2E)-1-(4-bromophenyl)-2-(2-chloro-6-fluorobenzylidene) hydrazine (0.300 g, 1.32 mmol) in benzene (10 mL) was added PCl5 (0.330 g, 1.58 mmol). The reaction mixture was stirred at RT for 18 h. The reaction mass was quenched in water, neutralized with NaHCO3 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.110 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.17 (d, J=8.7 Hz, 2H), 7.41 (d, J=8.7 Hz, 3H), 7.45-7.61 (m, 2H), 10.26 (s, 1H). MS (m/z): 361.34 (M−H)−.

後処理

  1. customThe reaction mass was quenched in water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-fe0ebf7c51b74e4b90c8a8e283a91012
出典データセット
uspto-grants-2016_09
特許番号
US09439890B2

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