Acetic Anhydride → HCID 178518031、化合物

HRID 1467419ノート

反応式

HRID 1467419 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-45debce6544442cb813a4272ceaedaf4
出典データセット
uspto-grants-2015_04
特許番号
US09000162B2

反応ノート

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