p-Toluenesulfonic acid → 3-Hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine

HRID 4440

反応式

HRID 4440 の反応式
C([O:4][CH2:5][C:6]1[C:7]([N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])=[N:8][CH:9]=[C:10]([CH:12]([Cl:14])[Cl:13])[N:11]=1)(=O)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OC)(=O)C>CO>[Cl:14][CH:12]([Cl:13])[C:10]1[N:11]=[C:6]([CH2:5][OH:4])[C:7]([N:15]2[C:19](=[O:20])[C:18]3=[CH:21][CH:22]=[CH:23][CH:24]=[C:17]3[C:16]2=[O:25])=[N:8][CH:9]=1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 6584Methyl AcetateHCID 136047763-Acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine

生成物 1

HCID 136047773-Hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine収率 54%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

A mixture of 15 g (0.04 mole) of 3-acetoxymethyl-5-dichloromethyl-2-phthalimidopyrazine, 150 ml of methanol and 0.15 g of p-toluenesulfonic acid was heated to the boil, and a mixture of methanol and methyl acetate was slowly distilled off in the course of 5 hours. The mixture was then evaporated down to one-third of its total volume, and the precipitated crystals were isolated, and recrystallized from ethyl acetate. 7.18 g (54%) of 5-dichloromethyl-3-hydroxymethyl-2-phthalimidopyrazine of melting point 188°-189° C. were obtained. 1H-NMR (CDCl3 270 MHz): δ4.7 (s, 2H), 6.9 (s, 1H), 8.1 (m, 4H), 9.1 (s, 1H).

後処理

  1. temperaturewas heated to the boil
  2. distillationwas slowly distilled off in the course of 5 hours
  3. customThe mixture was then evaporated down to one-third of its total volume
  4. customthe precipitated crystals were isolated
  5. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-25cf147f10cf48b9989fcb580416b649
出典データセット
uspto-grants-1988_02
特許番号
US04725689

関連ノート

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