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o-Phenylenediacetic acid → HCID 9909006, 화합물

HRID 1358756
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HRID 1358756 반응식
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][C:14]([OH:16])=O.[F:21][C:22]([S:25]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=1)(=[O:27])=[O:26])([F:24])[F:23]>ClCCl.CN(C=O)C.CN(C1C=CN=CC=1)C>[F:23][C:22]([F:21])([F:24])[S:25]([C:28]1[CH:29]=[C:30]([NH:34][C:14]([CH2:13][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:17][C:18]([OH:20])=[O:19])=[O:16])[CH:31]=[CH:32][CH:33]=1)(=[O:26])=[O:27]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 24123o-Phenylenediacetic acidHCID 65578Oxalyl chlorideHCID 27359433-Aminophenyl trifluoromethyl sulfone

생성물 1

HCID 9909006HCID 9909006, 화합물

시약·촉매·용매 3

HCID 6228Dimethylformamide촉매HCID 142844-(Dimethylamino)pyridine촉매
HCID 6344
Dichloromethane
용매

실험 절차

Oxalyl chloride (0.285 mL) was added to a solution of 1,2-phenylenediacetic acid (100 mg, 0.515 mmol) in dichloromethane, followed by 5 drops of DMF. The mixture was stirred at room temperature for 1.5 hours and cooled to 0° C. To the cooled mixture was added DMAP (63 mg, 0.62 mmol) and 3-aminophenyl trifluoromethyl sulfone (116 mg, 0.515 mmol). The mixture was allowed to warm to room temperature and extracted with ethyl acetate. The organic layer was washed with water, brine, dried and purified to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 11.31 (br s, 1H), 8.51 (s, 1H), 8.04 (m, 1H), 7.75 (d, J=5.1 Hz, 2H), 7.28 (m, 1H), 7.19 (m, 3H), 3.75 (s, 2H, CH2), 3.62 (s, 2H, CH2). MS 401.9 [M++1].

후처리

  1. temperaturecooled to 0° C
  2. temperatureto warm to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. custompurified

출처 및 근거

ORD 기록
ord-f2d76b5aeb89496db5757aee01cad1a3
출처 데이터셋
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06596772B1

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