Hydrochloric Acid → 4-Acetyl-2-fluorobenzene-1-sulfonamide

HRID 497261

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HRID 497261 반응식
[C:1]([C:4]1[CH:10]=[CH:9][C:7](N)=[C:6]([F:11])[CH:5]=1)(=[O:3])[CH3:2].Cl.[N+:13]([O-])([O-])=O.[Na+].[S:18](=[O:20])=[O:19]>O.C(O)(=O)C.O.O.[Cu](Cl)Cl>[C:1]([C:4]1[CH:10]=[CH:9][C:7]([S:18]([NH2:13])(=[O:20])=[O:19])=[C:6]([F:11])[CH:5]=1)(=[O:3])[CH3:2]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 24268Sodium NitrateHCID 30184631-(4-Amino-3-fluorophenyl)ethan-1-one

생성물 1

HCID 223169644-Acetyl-2-fluorobenzene-1-sulfonamide수율 46.6%

시약·촉매·용매 3

HCID 61482Cupric chloride dihydrate촉매HCID 176Acetic Acid용매HCID 962Water용매

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온도
0 °C

실험 절차

To a solution of 4-acetyl-2-fluoroaniline (5.0 g, 32.6 mmol, Krueger, G et al., Arzneim Forsch, 34, 11a, 1612 (1984)) in conc-HCl (24.0 mL), sodium nitrate (2.9 g, 42.4 mmol) in water (10 mL) was added at 0° C. After stirring for 1 h, the resultant yellow solution was added slowly to the suspension of copper (II) chloride dihydrate (1.7 g, 9.8 mmol) and sulfur dioxide (10 g, 156 mmol) in acetic acid (25 ml) at 0° C. The mixture was stirred for 30 min at 0° C. and poured into ice water (200 mL) and extracted with CH2Cl2 (80 mL×2). The extracts was cooled to 0° C. and 25% aqueous ammonia (70 mL) was added slowly and stirred for 1 h at room temperature. The mixture was concentrated and the residual solid was suspended with ether and collectted by filteration to give the title compound (3.3 g, 46%).

후처리

  1. stirringThe mixture was stirred for 30 min at 0° C.
  2. extractionextracted with CH2Cl2 (80 mL×2)
  3. addition25% aqueous ammonia (70 mL) was added slowly
  4. stirringstirred for 1 h at room temperature
  5. concentrationThe mixture was concentrated

출처 및 근거

ORD 기록
ord-81a220ba26cf4e4593f7307de0d41507
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949536B2

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