Sodium Hydroxide → 2-amino-5-chloro-N-(4-chlorophenyl)benzamide

HRID 370071

反応式

HRID 370071 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[N+:17]([O-])=O)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH2:17])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 873788Benzamide, 5-chloro-N-(4-chlorophenyl)-2-nitro-

生成物 1

HCID 41860192-amino-5-chloro-N-(4-chlorophenyl)benzamide収率 97.3%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
70 °C

実験手順

N-(4-Chlorophenyl)-5-chloro-2-nitrobenzamide (13.2 g, 42.4 mmol) and tin(II) chloride dihydrate (48 g, 213 mmol) were combined in ethyl acetate (90 mL) and the mixture was heated at 70° C. under a nitrogen atmosphere. After 15 minutes, the mixture was cooled to ambient temperature, then poured onto water (750 mL) and ethyl acetate (750 mL). The aqueous layer was adjusted to pH 8 with by addition of 1 N NaOH and a saturated NaHCO3 solution, and the layers were separated. The aqueous layer was further extracted with 500 mL of ethyl acetate. The combined organic extracts were washed with water (1 L), then brine (500 mL), dried over MgSO4, filtered, and concentrated in vacuo to afford 11.6 g (97% yield) of N-(4-chlorophenyl)-2-amino-5-chlorobenzamide as an off-white solid; NMR (CDCl3) 7.7 (br s, 1), 7.2-7.5 (m, 6), 6.7 (d, 1), 5.5 (br s, 2) ppm.

後処理

  1. temperaturethe mixture was cooled to ambient temperature
  2. customa saturated NaHCO3 solution, and the layers were separated
  3. extractionThe aqueous layer was further extracted with 500 mL of ethyl acetate
  4. washThe combined organic extracts were washed with water (1 L)
  5. dry with materialbrine (500 mL), dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-23338438eb864f45aba25de378658cdb
出典データセット
uspto-grants-2000_10
特許番号
US06140351

関連ノート

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