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Phosphorus oxychloride → 4-Chloro-5,7-difluoroquinazoline

HRID 1873646
ノート
印刷プレビュー

反応式

HRID 1873646 の反応式
P(Cl)(Cl)([Cl:3])=O.[F:6][C:7]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]2[C:8]=1[C:9](=O)[NH:10][CH:11]=[N:12]2.C(N(C(C)C)CC)(C)C>C(#N)C>[Cl:3][C:9]1[C:8]2[C:13](=[CH:14][C:15]([F:17])=[CH:16][C:7]=2[F:6])[N:12]=[CH:11][N:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24813Phosphorus oxychloride2 回HCID 81531DiisopropylethylamineHCID 1355106875,7-Difluoro-3,4-dihydroquinazolin-4-one

生成物 1

HCID 534026004-Chloro-5,7-difluoroquinazoline

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

Phosphoryl chloride (3.32 ml) was added to a stirred mixture of 5,7-difluoro-3,4-dihydroquinazolin-4-one (5 g), diisopropylethylamine (7.16 ml) and acetonitrile (120 ml) that was cooled in an ice bath. The resultant reaction mixture was heated to 80° C. for 2 hours. A second portion of phosphoryl chloride (1.52 ml) was added and the reaction mixture was heated to reflux for a further 2.75 hours to provide a solution of 4-chloro-5,7-difluoroquinazoline which was used without being isolated. A solution of 6-chloro-2,3-methylenedioxyaniline (International Application WO 01/94341, Example 17, Note [30]; 4.95 g) in acetonitrile (15 ml) was added and the reaction mixture was heated to 80° C. for 4 hours. The resultant reaction mixture was stirred at ambient temperature for 16 hours. A solution of a second portion of 6-chloro-2,3-methylenedioxyaniline (1.18 g) in acetonitrile (5 ml) was added and the reaction mixture was reheated to 80° C. for 1 hour. The reaction mixture was allowed to cool to ambient temperature and was stirred for one hour. The resultant slurry was filtered and the isolated solid was washed with acetonitrile (20 ml) and dried. There was thus obtained 4-(6-chloro-2,3-methylenedioxyanilino)-5,7-difluoroquinazoline as a mono-hydrochloride salt (7.88 g, 99.3% HPLC purity using Method A, retention time 4.46 minutes); NMR Spectrum: (DMSOd6) 5.5-6.0 (br s, 1H), 6.15 (s, 2H), 7.0 (d, 1H), 7.1 (d, 1H), 7.6 (d, 1H), 7.8 (m, 1H), 8.7 (s, 1H), 1.9-2.0 (m, 2H).

後処理

  1. temperaturewas cooled in an ice bath
  2. customThe resultant reaction mixture
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for a further 2.75 hours

出典と根拠

ORDレコード
ord-7518a70684d741d59fc66c450d9e9d48
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08304417B2

反応ノート

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