Pyridine → 2-(4-bromophenyl)-5-(2-chloro-6-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 508713ノート

反応式

HRID 508713 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][N:9]=[C:10]([C:12]2[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])[NH2:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:26](Cl)(Cl)=[O:27]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:26](=[O:27])[NH:11][C:10]([C:12]3[C:17]([F:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])=[N:9]2)=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 6371PhosgeneHCID 117965458N'-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonamide

生成物 1

HCID 1366448592-(4-bromophenyl)-5-(2-chloro-6-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
2.5 °C

実験手順

To a cold solution of N′-(4-bromophenyl)-2-chloro-6-fluorobenzenecarbohydrazonamide (0.050 g, 0.146 mmol) in CHCl3 was added pyridine (0.5 mL) and phosgene (1.0 mL) at 0-5° C. The reaction mass was stirred at 0-5° C. for 2-3 h. The reaction mass was quenched in water, neutralized with dilute acetic acid and extracted with DCM. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude product was purified with column chromatography on silica gel eluting with 1.0% MeOH:DCM to afford 0.020 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.50 (t, J=8.7 Hz, 1H), 7.56-7.71 (m, 4H), 7.89 (d, J=9.3 Hz, 2H), 12.69 (s, 1H). MS (m/z): 368.15 (M)+.

後処理

  1. customThe reaction mass was quenched in water
  2. extractionextracted with DCM
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe obtained crude product
  6. customwas purified with column chromatography on silica gel eluting with 1.0% MeOH

出典と根拠

ORDレコード
ord-f1f2c6c9390b4285a5a3e81983230a9b
出典データセット
uspto-grants-2015_08
特許番号
US09096545B2

反応ノート

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