Mecloqualone → 3-(2-Chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one

HRID 1169280

反応式

HRID 1169280 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH3:19].CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[C:9]1[CH:19]=[CH:22][N:23]([CH3:25])[CH3:24]

参加物

4

反応物 2

HCID 9567MecloqualoneHCID 78373Dimethylformamide dimethyl acetal2 回

生成物 1

HCID 536897693-(2-Chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one収率 62.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

A mixture of 3-(2-chloro-phenyl)-2-methyl-3,4-dihydro-quinazolin-4-one (1.0 g, 3.69 mmol) and dimethylformamide dimethyl acetal (0.64 mL, 4.8 mmol) in dimethylformamide (4 mL) was heated to 140° C. for 24 hours. Additional dimethylformamide dimethyl acetal (0.32 mL, 2.4 mmol) was added and heating was continued for an additional 24 hours. The reaction was cooled to ambient temperature and concentrated at reduced pressure (60° C. bath temperature). The dark residue was triturated with methanol and the pale orange solid which formed was collected and dried to give 0.75 g (62%) of 3-(2-chloro-phenyl)-2-(2-dimethylamino-vinyl)-3,4-dihydro-quinazolin-4-one which had: mp 228-230° C.; 1H 1H NMR δ 8.19 (d, J=8 Hz, 1H), 7.91 (d, J=12.3 Hz, 1H), 7.71-7.18 (m, 7H), 4.10 (d, J=12.3 Hz, 1H), 2.81 (br s, 6H). Analysis calculated for C18H16ClN3O: C, 66.36; H, 4.95; N, 12.90. Found: C, 66.20; H, 5.03; N, 12.79.

後処理

  1. temperatureheating
  2. temperatureThe reaction was cooled to ambient temperature
  3. concentrationconcentrated at reduced pressure (60° C. bath temperature)
  4. customThe dark residue was triturated with methanol
  5. customthe pale orange solid which formed
  6. customwas collected
  7. customdried

出典と根拠

ORDレコード
ord-a82b0769025d42b38648c587b336da1e
出典データセット
uspto-grants-2003_09
特許番号
US06627755B1

関連ノート

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