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

HRID 9346

반응식

HRID 9346 반응식
[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

참가 물질

5

반응물 3

HCID 115623-Bromoaniline2회HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 31214Ethyl orthoformate

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
55 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-25de6e20d68e4a01a05d61c43866a6f5
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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