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Dimethylamine → Sodium 5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

HRID 232418
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HRID 232418 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][S:13][C:14]3[CH:15]=[C:16]([CH:20]([S:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31])[S:21][CH2:22][CH2:23][C:24](O)=[O:25])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[I-].Cl[C:35]1C=CC=[CH:37][N+:36]=1C.CNC.[OH-].[Na+:46]>ClCCl.C(#N)C.C1(C)C=CC=CC=1.C(O)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][S:13][C:14]3[CH:15]=[C:16]([CH:20]([S:21][CH2:22][CH2:23][C:24](=[O:25])[N:36]([CH3:37])[CH3:35])[S:27][CH2:28][CH2:29][C:30]([O-:32])=[O:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[Na+:46]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

10

반응물 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 1670692-Chloro-1-methylpyridinium iodideHCID 104139205-(3-(7-Chloroquinolin-2-ylmethylthio)phenyl)-4,6-dithianonanedioic acid

생성물 1

HCID 23683603Sodium 5-(3-(7-chloroquinolin-2-ylmethylthio)phenyl)-8-dimethylcarbamyl-4,6-dithiaoctanoate

시약·촉매·용매 5

HCID 702
Ethanol
용매
HCID 1140Toluene용매
HCID 6342Acetonitrile용매
HCID 6344Dichloromethane용매
HCID 8471Triethylamine용매

실험 절차

To a solution of diacid (Step 4) (360 mg) in dichloromethane (28 mL) and acetonitrile (7.1 mL) was added 2-chloro-1-methylpyridinium iodide (227 mg). The solution was cooled to 0 C. and triethylamine (123 μL) was added. After stirring for 15 min, 0.42 mL of a 2M solution of dimethylamine in toluene was added. The solution was stirred 1 hr at room temperature, washed with acidified 25% ammonium acetate, dried over sodium sulfate, filtered and evaporated to dryness. To the oil obtained after chromatography, in 2 mL of ethanol, was added 0.154 mL of 2N NaOH. After evaporating to dryness the title compound was obtained as a foam.

후처리

  1. temperatureThe solution was cooled to 0 C
  2. stirringThe solution was stirred 1 hr at room temperature
  3. washwashed
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customTo the oil obtained after chromatography
  8. customAfter evaporating to dryness the title compound
  9. customwas obtained as a foam

출처 및 근거

ORD 기록
ord-5f7a9d445a1041dabcc8883dae5be96b
출처 데이터셋
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04851409

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