Chloroacetonitrile → 7-Cyanomethyl-3-methyl-xanthine

HRID 1904902

반응식

HRID 1904902 반응식
[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]

참가 물질

5

반응물 2

HCID 7856ChloroacetonitrileHCID 706393-Methylxanthine

생성물 1

HCID 147484527-Cyanomethyl-3-methyl-xanthine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3b3dc456fb3e4ad9b26a410454eafcd3
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04840949

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