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Pyridine → 2-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide

HRID 424176
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HRID 424176 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:20]([CH3:19])(=[O:22])=[O:21])=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:10])=[O:11]
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참가 물질

5

반응물 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 218887652,5-Diaminobenzenesulfonamide

생성물 1

HCID 249506572-Amino-5-[(methylsulfonyl)amino]benzenesulfonamide수율 73.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
23 °C

실험 절차

2,5-Diamino-benzenesulfonamide (4.20 kg, 22.4 mol) was dissolved in dichloromethane (120 L) and pyridine (8.00 kg, 89.9 mol), and the resulting solution was cooled to 0° C. Methanesulfonyl chloride (2.80 kg, 24.4 mol) was added slowly, and the resulting mixture was allowed to warm to 23° C. and stirred for 2 days. The mixture was filtered and the resulting solid was washed with dichloromethane (2×20 L). The solid was diluted with water (100 L) and 1.0 M aqueous hydrochloric acid solution (25 L), and was then stirred at 23° C. for 1 h. The mixture was filtered and the resulting solid was washed with water (20 L) and then with methyl-tert-butyl ether (2×10 L). The solid was further dried in vacuo at 45° C. to afford the desired product, 2-amino-5-methanesulfonylamino-benzenesulfonamide (4.39 kg, 16.5 mol, 73%) as a pale pink solid. 1H NMR (400 MHz, CD3OD) δ: 2.89 (3H, s), 6.82 (1H, d, J=8.5 Hz), 7.20 (1H, dd, J1=8.5 Hz, J2=2.5 Hz), 7.58 (1H, d, J=2.5 Hz). LC-MS (ESI) calcd for C7H11N3O4S2 265.02, found 266.0 [M+H+].

후처리

  1. filtrationThe mixture was filtered
  2. washthe resulting solid was washed with dichloromethane (2×20 L)
  3. additionThe solid was diluted with water (100 L) and 1.0 M aqueous hydrochloric acid solution (25 L)
  4. stirringwas then stirred at 23° C. for 1 h
  5. filtrationThe mixture was filtered
  6. washthe resulting solid was washed with water (20 L)
  7. customThe solid was further dried in vacuo at 45° C.

출처 및 근거

ORD 기록
ord-b29eb93d59ee4a5a8e224f7ae9eb8f2c
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08101800B2

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