N,N-Dimethylaniline → 4-Chloro-2-(2-methoxy-6-methyl-phenyl)-7-methyl-quinazoline

HRID 2079316ノート

反応式

HRID 2079316 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[C:10]1[NH:19][C:18](=O)[C:17]2[C:12](=[CH:13][C:14]([CH3:21])=[CH:15][CH:16]=2)[N:11]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:33].C([O-])(O)=O.[Na+]>C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:33][C:18]1[C:17]2[C:12](=[CH:13][C:14]([CH3:21])=[CH:15][CH:16]=2)[N:11]=[C:10]([C:4]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:19]=1

参加物

7

反応物 4

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1361213362-(2-methoxy-6-methyl-phenyl)-7-methyl-3H-quinazolin-4-one

生成物 1

HCID 580107904-Chloro-2-(2-methoxy-6-methyl-phenyl)-7-methyl-quinazoline収率 99.1%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 1140Toluene溶媒

実験手順

2-(2-Methoxy-6-methyl-phenyl)-7-methyl-3H-quinazolin-4-one (1.61 g, 5.74 mmol) was suspended in benzene after which was added N,N-dimethylaniline (1.1 mL, 8.62 mmol) and POCl3 (1.61 mL, 17.27 mmol). The reaction mixture was refluxed for 3 hours during which the color changed from yellow to dark red. The reaction mixture was cooled to room temperature, diluted with 40 mL toluene and poured onto ice. Saturated aq. NaHCO3 was carefully added until the pH remained constant at 7 and no more gas formed. The layers were separated, and the water layer was extracted with toluene. The organic layers were combined and washed with respectively 50 mL saturated aq. NaCl, 60 mL 0.5 N HCl, 40 mL 5% NaHCO3 and 50 mL saturated aq. NaCl. The solution was dried over Na2SO4 and evaporated to dryness to yield 1.7 g of the impure product. The product was filtered through silica gel and washed with CH2Cl2:heptane (2:1) to yield of 4-chloro-2-(2-methoxy-6-methyl-phenyl)-7-methyl-quinazoline (1.22 g, 71%).

後処理

  1. temperatureThe reaction mixture was refluxed for 3 hours during which the color
  2. additionpoured onto ice
  3. customno more gas formed
  4. customThe layers were separated
  5. extractionthe water layer was extracted with toluene
  6. washwashed with respectively 50 mL saturated aq. NaCl, 60 mL 0.5 N HCl, 40 mL 5% NaHCO3 and 50 mL saturated aq. NaCl
  7. dry with materialThe solution was dried over Na2SO4
  8. customevaporated to dryness

出典と根拠

ORDレコード
ord-18318438fc804f1da79a09e05245d794
出典データセット
uspto-grants-2011_04
特許番号
US07928107B2

反応ノート

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