Chloroacetonitrile → 7-Cyanomethyl-3-methyl-xanthine

HRID 1904902

反応式

HRID 1904902 の反応式
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].Cl[CH2:14][C:15]#[N:16]>[OH-].[Na+].CN(C)C=O>[C:15]([CH2:14][N:7]1[C:6]2[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1)#[N:16]

参加物

5

反応物 2

HCID 7856ChloroacetonitrileHCID 706393-Methylxanthine

生成物 1

HCID 147484527-Cyanomethyl-3-methyl-xanthine

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 14798Sodium Hydroxide溶媒

実験手順

35.0 g (0.25 mole) of 3-methyl-xanthine (Chem. Ber. 83, 209 1950) are dissolved in 81.4 ml (0.25 mole) of a 10% sodium hydroxide solution under shaking; crystallization takes place within some minutes. Water is distilled off in vacuo and the traces of water are removed by azeotropic distillation with toluene. The residue is suspended in 35 ml of dimethyl formamide, whereupon a solution of 18.9 g (0.25 mole) of chloroacetonitrile in 80 ml of dimethyl formamide is added dropwise at 100° C. within 30 minutes. The reaction mixture is stirred at 100° C. for a further hour, filtered until hot, the precipitate (sodium chloride) is washed with hot dimethyl formamide and the united solutions are evaporated to dryness under reduced pressure. The residue is treated with 100 ml of acetone, the crystals are filtered by suction and throughly washed with acetone. The 7-cyanomethyl-3-methyl-xanthine (m.p.: 285°-287° C.) thus obtained can be used in further reactions.

後処理

  1. customcrystallization
  2. distillationWater is distilled off in vacuo
  3. customthe traces of water are removed by azeotropic distillation with toluene
  4. additionis added dropwise at 100° C. within 30 minutes
  5. stirringThe reaction mixture is stirred at 100° C. for a further hour
  6. filtrationfiltered until hot, the precipitate (sodium chloride)
  7. washis washed with hot dimethyl formamide
  8. customthe united solutions are evaporated to dryness under reduced pressure
  9. additionThe residue is treated with 100 ml of acetone
  10. filtrationthe crystals are filtered by suction
  11. washthroughly washed with acetone

出典と根拠

ORDレコード
ord-3b3dc456fb3e4ad9b26a410454eafcd3
出典データセット
uspto-grants-1989_06
特許番号
US04840949

関連ノート

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