Isopropylamine → 2-Chloro-4-isopropylamino-6-nitroquinazoline

HRID 1250582

反応式

HRID 1250582 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=O)[NH:8][C:7]2=O)([O-:3])=[O:2].P(Cl)(Cl)([Cl:18])=O.[CH:21]([N:24](C(C)C)C=O)([CH3:23])[CH3:22].C(N)(C)C>O>[Cl:18][C:9]1[N:8]=[C:7]([NH:24][CH:21]([CH3:23])[CH3:22])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:10]=1

参加物

6

反応物 4

HCID 6363IsopropylamineHCID 24813Phosphorus oxychlorideHCID 75912N,N-bis(1-methylethyl)formamideHCID 8169826-Nitro-2,4(1H,3H)-quinazolinedione

生成物 1

HCID 183264282-Chloro-4-isopropylamino-6-nitroquinazoline収率 67.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To 1.00 g (4.83 mmol) of 6-nitroquinazoline-2,4 (1H,3H)-dione were added 32.90 g (0.22 mol) of phosphorus oxychloride and 0.70 ml (4.83 mmol) of diisopropylformamide, and the resulting mixture was subjected to heating under reflux for 24 hours. After phosphorus oxychloride was removed in vacuo, the mixture was dissolved in 15 ml of acetonitrile, followed by addition of 2.49 ml (29.11 mmol) of isopropylamine under ice cooling and stirring under ice cooling for 30 minutes. To the reaction solution was added water, followed by extraction with ethyl acetate, washing with brine and drying over anhydrous sodium sulfate. After the solvent was distilled off, the residue was purified by a silica gel column to give 870 mg (yield: 67.5%) of the title compound.

後処理

  1. temperatureto heating
  2. temperatureunder reflux for 24 hours
  3. customAfter phosphorus oxychloride was removed in vacuo
  4. dissolutionthe mixture was dissolved in 15 ml of acetonitrile
  5. extractionfollowed by extraction with ethyl acetate
  6. washwashing with brine
  7. dry with materialdrying over anhydrous sodium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe residue was purified by a silica gel column

出典と根拠

ORDレコード
ord-f116485c5cf24fc8b6a0f56ed644b8b4
出典データセット
uspto-grants-2002_01
特許番号
US06339089B2

関連ノート

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