Diisopropylethylamine → 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

HRID 394188ノート

反応式

HRID 394188 の反応式
C(N(C(C)C)CC)(C)C.Br[C:11]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[C:36]([Br:43])[C:12]=1[CH2:13][N:14]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34]C)=[CH:29][CH:28]=1)[C:15]([NH:17][C:18]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:25])=[O:16]>CN(C=O)C.[Cu]I>[Br:43][C:36]1[CH:37]=[C:38]([N+:40]([O-:42])=[O:41])[CH:39]=[C:11]2[C:12]=1[CH2:13][N:14]([CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)[C:15](=[O:16])[N:17]2[C:18]1[C:19]([Cl:25])=[CH:20][CH:21]=[CH:22][C:23]=1[Cl:24]

参加物

5

反応物 2

HCID 81531DiisopropylethylamineHCID 22648032N-(2,6-dibromo-4-nitrobenzyl)-N'-(2,6-dichlorophenyl)-N-(4-ethoxybenzyl)urea

生成物 1

HCID 226481455-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

Diisopropylethylamine (1.78 g, 13.8 mmol) and CuI (2.63 g, 13.8 mmol) was added to N-(2,6-dibromo-4-nitrobenzyl)-N′-(2,6-dichlorophenyl)-N-(4-ethoxybenzyl)urea (4.25 g, 6.88 mmol) in DMF (150 mL). After evacuating and flushing three times with argon, the reaction mixture was heated to 130° C. for 3 h, cooled to rt, and filtered. The filtrate was concentrated under reduced pressure and purified by flash chromatography on Biotage 40M columns, eluting with 80:20 hexanes-acetone to yield 5-bromo-1-(2,6-dichlorophenyl)-3-(4-methoxybenzyl)-7-nitro-3,4-dihydroquinazolin-2(1H)-one. Mass spectrum (ESI) 536.0 (M+1).

後処理

  1. customAfter evacuating
  2. customflushing three times with argon
  3. temperaturecooled to rt
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography on Biotage 40M columns
  7. washeluting with 80:20 hexanes-acetone

出典と根拠

ORDレコード
ord-797a6050d93b4dbd846880fffb77b996
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

反応ノート

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