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Water → HCID 22908984, 화합물

HRID 1378978
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HRID 1378978 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:31](O)(=[O:33])=[O:32])[C:6](=[CH:27][C:28]=1[O:29][CH3:30])/[CH:7]=[CH:8]/[C:9]1[N:17]([CH3:18])[C:16]2[C:15](=[O:19])[N:14]([CH2:20][CH2:21][CH3:22])[C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH3:26])[C:11]=2[N:10]=1.S(Cl)(Cl)=O.[CH2:39]([NH:41][CH2:42][CH3:43])[CH3:40].O>CN(C)C=O>[CH2:39]([N:41]([CH2:42][CH3:43])[S:31]([C:5]1[C:6](=[CH:27][C:28]([O:29][CH3:30])=[C:3]([O:2][CH3:1])[CH:4]=1)/[CH:7]=[CH:8]/[C:9]1[N:17]([CH3:18])[C:16]2[C:15](=[O:19])[N:14]([CH2:20][CH2:21][CH3:22])[C:13](=[O:23])[N:12]([CH2:24][CH2:25][CH3:26])[C:11]=2[N:10]=1)(=[O:32])=[O:33])[CH3:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 962WaterHCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 22909004HCID 22909004, 화합물

생성물 1

HCID 22908984HCID 22908984, 화합물수율 30%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Compound 1 (1.00 g, 1.96 mmol) obtained in Example 1 was dissolved in 20 ml of dimethylformamide. To the solution was dropwise added 0.29 ml (3.92 mmol) of thionyl chloride under ice-cooling, and the resulting mixture was stirred at room temperature for 10 minutes. After ice-cooling, 1.02 ml (9.80 mmol) of diethylamine was added dropwise to the mixture, and the resulting mixture was stirred at room temperature for one hour. The mixture was poured into 50 ml of water and extracted three times with 20 ml of chloroform. The extract was washed successively with water and a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by column chromatography (eluent: 65% ethyl acetate/hexane), followed by recrystallization from cyclohexane/toluene to give 320 mg (yield 30%) of Compound 2 as a pale yellow powder.

후처리

  1. temperaturecooling
  2. temperatureAfter ice-cooling
  3. stirringthe resulting mixture was stirred at room temperature for one hour
  4. extractionextracted three times with 20 ml of chloroform
  5. washThe extract was washed successively with water
  6. dry with materiala saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate
  7. customfollowed by evaporation under reduced pressure
  8. customThe residue was purified by column chromatography (eluent: 65% ethyl acetate/hexane)
  9. customfollowed by recrystallization from cyclohexane/toluene

출처 및 근거

ORD 기록
ord-8b20f65acdf745148e73e0d98b6f82d8
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05670498

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