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Triethylamine → HCID 90462565, 화합물

HRID 588853
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HRID 588853 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:18][CH:17]3[CH:13]([CH2:14][NH:15][CH2:16]3)[CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].CCN([CH2:24][CH3:25])CC.[S:26](Cl)(Cl)(=[O:28])=[O:27]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([N:11]2[CH2:12][CH:13]3[CH:17]([CH2:16][N:15]([S:26]([CH:24]=[CH2:25])(=[O:28])=[O:27])[CH2:14]3)[CH2:18]2)=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 66211026HCID 66211026, 화합물

생성물 1

HCID 90462565HCID 90462565, 화합물수율 11%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3,4-dichlorophenyl)(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)methanone (100 mg, 0.35 mmol) in DCM (10 mL) at 0° C., Et3N (106 mg, 1 mmol) was added followed by sulfonyl chloride (60 mg, 0.37 mmol). The resulting mixture was stirred at room temperature overnight. The mixture was partitioned between DCM and water. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by Isolera One (silica gel cartridge, 10-100% ethyl acetate/hexanes) to afford the desired product (14 mg, 11%). 1H NMR (300 MHz, CDCl3) δ: 7.60 (d, J=2.0 Hz, 1H), 7.51 (d, J=8.2 Hz, 1H), 7.35 (dd, J=2.0, 8.2 Hz, 1H), 6.50 (dd, J=9.9, 16.5 Hz, 1H), 6.30 (d, J=16.6 Hz, 1H), 6.09 (d, J=9.9 Hz, 1H), 2.90-4.10 (m, 10H). ESI-MS m/z: 375.0[M+H]+.

후처리

  1. customThe mixture was partitioned between DCM and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by Isolera One (silica gel cartridge, 10-100% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-cbe8797e18f648c8856604afa3116b95
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09227978B2

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