Benzenamine, 2-bromo-4-nitro- → 3-(2-Bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione

HRID 1071746

反応式

HRID 1071746 の反応式
[N:1]([C:4]1[CH:13]=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8]C)=O)=[C:2]=[O:3].[Br:14][C:15]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:16]=1[NH2:17].CCN(C(C)C)C(C)C.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[Br:14][C:15]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:16]=1[N:17]1[C:6](=[O:8])[C:5]2[C:4](=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:1][C:2]1=[O:3]

参加物

6

反応物 4

HCID 25840Benzenamine, 2-bromo-4-nitro-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81531DiisopropylethylamineHCID 519494Methyl 2-isocyanatobenzoate

生成物 1

HCID 220644013-(2-Bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione収率 44.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 2-isocyanatobenzoate (0.266 g, 1.5 mmol) and 2-bromo-4-nitroaniline (0.325 g, 1.5 mmol) in DMF (2 mL) was added DIEA (0.79 mL). The reaction mixture was stirred at room temp for 24 hr, with addition of DBU (0.22 mL) at 17 hr. The reaction mixture was extracted with EtOAc, washed with 1 N HCl and brine, dried and concentrated to give crude product, which was chromatographed on silica gel with 10% EtOAc/CH2Cl2 to give 3-(2-bromo-4-nitrophenyl)-1,3-dihydroquinazoline-2,4-dione (0.24 g, 44%). ES-MS (M+H)+=362, 364 (Br).

後処理

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washwashed with 1 N HCl and brine
  3. customdried
  4. concentrationconcentrated
  5. customto give crude product, which
  6. customwas chromatographed on silica gel with 10% EtOAc/CH2Cl2

出典と根拠

ORDレコード
ord-e9b92a9ff470427bb9eb9f9325b7460f
出典データセット
uspto-grants-2005_06
特許番号
US06906063B2

関連ノート

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