Water → {4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

HRID 605296ノート

反応式

HRID 605296 の反応式
[Cl:1][C:2]([Cl:35])([Cl:34])[CH2:3][O:4][C:5](=[O:33])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[N+:30]([O-])=O)=[CH:9][CH:8]=1.[Cl-].[NH4+].O1CCCC1.O>C(O)C.[Fe]>[Cl:35][C:2]([Cl:1])([Cl:34])[CH2:3][O:4][C:5](=[O:33])[NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:29])[NH:21][C:22]3[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=3)=[CH:16][C:15]=2[NH2:30])=[CH:11][CH:12]=1

参加物

7

反応物 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 67040283{4-[4-(4-Bromo-phenylcarbamoyl)-2-nitro-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester

生成物 1

HCID 67040452{4-[2-Amino-4-(4-bromo-phenylcarbamoyl)-phenoxy]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester収率 42%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

実験手順

The product from Example 268B (6.0 g, 10 mmol), iron powder (2.8 g, 50 mmol) and ammonium chloride (0.81 g, 15 mmol) in a mixture of ethanol (60 mL), tetrahydrofuran (60 mL), and water (20 mL) was heated under reflux for 5 hours and then cooled to room temperature. The reaction mixture was filtered through Celite and the filter pad was rinsed with ethanol (100 mL). The filtrate was evaporated under reduced pressure to leave a residue which was triturated with hexanes/ethyl acetate 4/1 to provide the title product (2.39 g, 42%) as a tan solid.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe filter pad was rinsed with ethanol (100 mL)
  5. customThe filtrate was evaporated under reduced pressure
  6. customto leave a residue which
  7. customwas triturated with hexanes/ethyl acetate 4/1

出典と根拠

ORDレコード
ord-48e664271e1e422189aade1c72221acf
出典データセット
uspto-grants-2011_03
特許番号
US07910595B2

反応ノート

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