Acetic Acid → 3-Hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine

HRID 4444

반응식

HRID 4444 반응식
[C:1]([OH:4])(=O)[CH3:2].C([O-])(=O)C.[K+].ClCC1[C:13]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])=[N:14][CH:15]=[C:16]([CH:18]([Cl:20])[Cl:19])[N:17]=1.ClCCl>CS(C)=O.O>[Cl:20][CH:18]([Cl:19])[C:16]1[N:17]=[C:2]([CH2:1][OH:4])[C:13]([N:21]2[C:25](=[O:26])[C:24]3=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]3[C:22]2=[O:31])=[N:14][CH:15]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 517044Potassium AcetateHCID 136047693-Chloromethyl-5-dichloromethyl-2-phthalimidopyrazine

생성물 1

HCID 136047773-Hydroxymethyl-5-dichloromethyl-2-phthalimidopyrazine수율 47%

시약·촉매·용매 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)용매

실험 절차

50 ml of glacial acetic acid and 35 g of potassium acetate were added to a solution of 57.7 g (0.16 mole) of 65% strength 3-chloromethyl-5-dichloromethyl-2-phthalimidopyrazine in 1,000 ml of a 95:5 dimethyl sulfoxide/water mixture. The mixture was stirred for three days at room temperature, after which 1,000 ml of dichloromethane and 1,000 ml of ice-water were added, the resulting mixture was mixed thoroughly and phase separation was effected. The aqueous phase was washed once with 500 ml of dichloromethane and once with 250 ml of dichloromethane, and the combined organic phases were washed twice with 1,000 ml of water, dried over sodium sulfate and evaporated down. The resulting black oil was brought to crystallization with 50 ml of methanol, and then recrystallized from 700 ml of methanol. 16.6 g (47%) of 5-dichloromethyl-3-hydroxymethyl-2-phthalimidopyrazine of melting point 191°-192° C. (sublimation with decomposition) were obtained. 1H-NMR (200 MHz, CDCl3): δ3.3 (t, OH), 4.8 (d, 2H), 6.9 (s, 1H), 8.0 (m, 4H), 9.1 (s, 1H).

후처리

  1. additionthe resulting mixture was mixed thoroughly
  2. customphase separation
  3. washThe aqueous phase was washed once with 500 ml of dichloromethane and once with 250 ml of dichloromethane
  4. washthe combined organic phases were washed twice with 1,000 ml of water
  5. dry with materialdried over sodium sulfate
  6. customevaporated down
  7. customThe resulting black oil was brought to crystallization with 50 ml of methanol
  8. customrecrystallized from 700 ml of methanol

출처 및 근거

ORD 기록
ord-e68e567d6ece4a128886cf5a849df771
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725689

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