Benzene, 1-fluoro-4-[(4-nitrophenyl)sulfonyl]- → 4-((4-Fluorophenyl)sulfonyl)aniline

HRID 1795784노트

반응식

HRID 1795784 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-])=O>CO.[Rh]>[F:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

참가 물질

4

반응물 1

HCID 22179363Benzene, 1-fluoro-4-[(4-nitrophenyl)sulfonyl]-

생성물 1

HCID 5728144-((4-Fluorophenyl)sulfonyl)aniline

시약·촉매·용매 2

HCID 23948Rhodium촉매HCID 887Methanol용매

실험 절차

A mixture of 4-fluorophenyl 4-nitrophenyl sulfone (1.89 g, 6.72 mmol) in methanol (80 mL) is treated with Rhodium on carbon (5%, 95 mg) and hydrogenated at 20 psi for 24 hr. The mixture is filtered, rinsing with methylene chloride (2×100 mL) and methanol (100 mL). The filtrate is concentrated to near dryness and refiltered, rinsing with minimal methanol. The solid is dried in the vacuum oven at 500 to give the desired amine, mp=204–205°: IR (drift) 3473, 3373, 1638, 1592, 1489, 1303, 1294, 1285, 1231, 1159, 1144, 1107, 834, 713 and 689 cm−1; NMR (300 MHz, CDCl3) 7.80–7.95, 7.60–7.75, 7.13, 6.60–6.75 and 4.17 δ; MS (EI) m/z 251 (M+), 140, 108, 95, 92, 80, 65, 65, 63 and 51.

후처리

  1. filtrationThe mixture is filtered
  2. washrinsing with methylene chloride (2×100 mL) and methanol (100 mL)
  3. concentrationThe filtrate is concentrated
  4. washrinsing with minimal methanol
  5. customThe solid is dried in the vacuum oven at 500

출처 및 근거

ORD 기록
ord-913f6153aad24f5c9468b43c8927d2bf
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030109B2

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