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p-Toluenesulfonic acid monohydrate → HCID 135939043, 화합물

HRID 591704
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인쇄 미리보기

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HRID 591704 반응식
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:5][CH:4]=1)=O.[NH2:14][C:15]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[C:16]=1[C:17]([NH2:19])=[O:18].OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1.O>CC(N(C)C)=O.CCOC(C)=O>[CH3:27][O:26][C:20]1[CH:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:15]2[C:16]=1[C:17](=[O:18])[NH:19][C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[CH:5][CH:4]=1)=[N:14]2
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참가 물질

7

반응물 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 189253554-(Methylsulfonylamino)benzaldehydeHCID 203490162-Amino-4,6-dimethoxybenzamideHCID 23665763Sodium Bisulfite

생성물 1

HCID 135939043HCID 135939043, 화합물수율 113.5%

시약·촉매·용매 2

HCID 8857
Ethyl Acetate
용매
HCID 31374Dimethylacetamide용매

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온도
155 °C

실험 절차

A mixture of N-(4-formylphenyl)methanesulfonamide (0.161 g, 0.0800 mmol), 2-amino-4,6-dimethoxybenzamide (0.159 g, 0.0800 mmol), NaHSO3 (94%, 0.00460 g, 0.0240 mmol), and p-TsOH.H2O (0.0125 g, 0.120 mmol) in DMA (1.00 mL) was heated at 155° C. for 16 hours. The mixture was diluted with EtOAc (50 mL), washed with water (2×50 mL), then brine (50 mL), dried over Na2SO4, filtered, and the solvent was removed under vacuum. The residue was purified over silica gel (12 g, CH2Cl2/MeOH) and the product was freeze-dried from MeCN/H2O to provide the title compound (0.0341 g, 11%) as a pale yellow solid. 1H NMR (300 MHz, DMSO-d6): δ 11.94 (s, 1H), 10.21 (s, 1H), 8.16 (d, J=8.76 Hz, 2H), 7.30 (d, J=8.76 Hz, 2H), 6.72 (d, J=2.25 Hz, 1H), 6.52 (d, J=2.25 Hz, 1H), 3.89 (s, 3H), 3.85 (s, 3H), 3.09 (s, 3H). MS (ESI) m/z 376 [C17H17N3O5S+H]+.

후처리

  1. washwashed with water (2×50 mL)
  2. dry with materialbrine (50 mL), dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum
  5. customThe residue was purified over silica gel (12 g, CH2Cl2/MeOH)
  6. dry with materialthe product was freeze-dried from MeCN/H2O

출처 및 근거

ORD 기록
ord-47d5815fe3904d528b3727dc6c509f6d
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238640B2

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