3-Bromoaniline → 5-((3-Bromophenylamino)methylene)-2,2-di-methyl-1,3-dioxane-4,6-dione

HRID 9346

反応式

HRID 9346 の反応式
[CH:1](OCC)(OCC)OCC.[CH3:11][C:12]1([CH3:20])[O:19][C:17](=[O:18])[CH2:16][C:14](=[O:15])[O:13]1.[Br:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>C(O)C>[Br:21][C:22]1[CH:23]=[C:24]([NH:25][CH:1]=[C:16]2[C:17](=[O:18])[O:19][C:12]([CH3:20])([CH3:11])[O:13][C:14]2=[O:15])[CH:26]=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 115623-Bromoaniline2 回HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformate

生成物 1

HCID 172522195-((3-Bromophenylamino)methylene)-2,2-di-methyl-1,3-dioxane-4,6-dione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
55 °C

実験手順

A mixture of triethyl orthoformate (154 grams (g), 1.04 moles (mol) and Meldrum's acid (142 g, 0.983 mol) was heated to 55° C. for 4 hours (h). After cooling to 50° C., a solution of 3-bromoaniline (162.6 g, 0.945 mol) in ethanol (300 mL) was added such that the temperature of the reaction was maintained between 50–55° C. After half of the 3-bromoaniline had been added, stirring became difficult due to the formation of solids, so more ethanol (1 liter (L)) was added to facilitate stirring. Upon complete addition, the reaction was cooled to room temperature (RT), and the solids were collected by filtration. The filter cake was washed with ice cold ethanol until the washings were nearly colorless, and the product was dried at 65° C. under vacuum to afford 287 g of 5-[(3-bromophenylamino)methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione as an off-white solid.

後処理

  1. temperatureAfter cooling to 50° C.
  2. temperaturewas maintained between 50–55° C
  3. additionwas added
  4. stirringto facilitate stirring
  5. additionUpon complete addition
  6. temperaturethe reaction was cooled to room temperature (RT)
  7. filtrationthe solids were collected by filtration
  8. washThe filter cake was washed with ice cold ethanol until the washings
  9. customthe product was dried at 65° C. under vacuum

出典と根拠

ORDレコード
ord-25de6e20d68e4a01a05d61c43866a6f5
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

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