Acetic Anhydride → HCID 178518031、化合物

HRID 2386921ノート

反応式

HRID 2386921 の反応式
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]([F:12])[C:3]=1[C:4]([NH2:6])=[O:5].S([O-])([O-])(=O)=O.[NH4+].[NH4+].[CH2:20](OC(OCC)OCC)C.C(OC(=O)C)(=O)C>>[F:12][C:7]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]2[C:3]=1[C:4]([OH:5])=[N:6][CH:20]=[N:1]2

参加物

5

反応物 4

HCID 7918Acetic AnhydrideHCID 31214Ethyl orthoformateHCID 6097028Ammonium SulfateHCID 592230322-Amino-3,6-difluorobenzamide

生成物 1

HCID 178518031HCID 178518031、化合物収率 92.3%

反応条件

温度
145 °C

実験手順

2-Amino-3,6-difluorobenzamide (2.0 g, 11.6 mmol), ammonium sulfate (0.15 g, 1.16 mmol), triethylorthoformate (4.3 g, 4.8 mL, 29.1 mmol) and acetic anhydride (3.0 g, 2.8 mL, 29.1 mmol) were combined in a 100 mL round bottomed flask and the mixture heated to 145° C. on a heating mantle, becoming nearly homogeneous around 90° C., then precipitating additional solid. After 1 h, the mixture was cooled to room temperature and diluted with water and stirred. The precipitated solids were collected by filtration, washed with water and dried to give 1.95 g of 5,8-difluoroquinazolin-4-ol as a white solid. A second crop of 0.13 g was collected from the cold concentrated filtrate, 98% overall. M.P. 257-258° C., LC/MS (ESI) m/z 182, 1H NMR (300 MHz, d6-DMSO) δ 12.48 (bs, 1H), 8.13 (s, 1H), 7.70 (m, 1H), 7.27 (m, 1H).

後処理

  1. custombecoming nearly homogeneous around 90° C.
  2. customprecipitating additional solid
  3. temperaturethe mixture was cooled to room temperature
  4. additiondiluted with water
  5. filtrationThe precipitated solids were collected by filtration
  6. washwashed with water
  7. customdried

出典と根拠

ORDレコード
ord-dea32cc2f9744080b42fd26defc94522
出典データセット
uspto-grants-2012_09
特許番号
US08268843B2

反応ノート

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