3-Chlorobenzoic Acid → 4-[4-(4-Fluorophenyl)-1,1-dimethylcyclopenta-2,4-dien-3-yl]benzenesulfonamide

HRID 1901106

반응식

HRID 1901106 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]=2[C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=O.ClC1C=C(C=CC=1)C(O)=O.C([O-])(=O)C.[Na+]>ClCCl.C(O)(=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:15]3[CH:16]=[CH:17][C:18]([S:21]([NH2:24])(=[O:22])=[O:23])=[CH:19][CH:20]=3)=[CH:10][C:11]([CH3:14])([CH3:13])[CH:12]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 4473-Chlorobenzoic AcidHCID 70297m-Chloroperbenzoic acidHCID 517045Sodium AcetateHCID 102690884-[2(4-Fluorophenyl)-4,4-dimethylcyclopenten-1-yl)benzenesulfonamide

생성물 1

HCID 101545054-[4-(4-Fluorophenyl)-1,1-dimethylcyclopenta-2,4-dien-3-yl]benzenesulfonamide수율 67%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1.0 g (2.89 mmol) of 4-[2-(4-fluorophenyl) -4,4-dimethylcyclopenten-1-yl)benzenesulfonamide (from Step 2) in 20 mL of dichloromethane was treated with 800 mg (80% peroxyacid, 3.7 mmol ) of m-chloroperoxybenzoic acid (MCPBA). The reaction was stirred at ambient temperature for 3 hours, washed with aqueous saturated sodium bisulfite, dried (MgSO4), and concentrated in vacuo to give a mixture of desired expoxide intermediate and m-chlorobenzoic acid; this crude mixture in 15 mL of acetic acid and 2 mL of water was subsequently treated with 1.0 g (12.2 mmol) of sodium acetate and stirred at 80° C. for 15 hours. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between water and ethyl acetate; the organic phase was washed with aqueous saturated sodium bicarbonate, water, brine, dried (MgSO4), and reconcentrated in vacuo. Purification by silica gel chromatography gave 665 mg (67%) of 4-[4-(4-fluorophenyl)-1,1-dimethylcyclopenta-2,4-dien-3-yl]benzenesulfonamide as a colorless solid: mp 163.5°-164.5° C. (dec); NMR (CDCl3) d 1.33 (s, 6H), 4.83 (br s, 2H), 6.34 (d, J=2 Hz, 1H), 6.45 (d, J=2 Hz, 1H), 6.94 (t, J=9 Hz, 2H), 7.00-7.20 (m, 2H), 7.25 (d, J=8 Hz, 2H), 7.78 (d, J=8 Hz, 2H).

후처리

  1. washwashed with aqueous saturated sodium bisulfite
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto give
  5. stirringstirred at 80° C. for 15 hours
  6. temperatureThe reaction mixture was cooled to ambient temperature
  7. concentrationconcentrated in vacuo
  8. customThe residue was partitioned between water and ethyl acetate
  9. washthe organic phase was washed with aqueous saturated sodium bicarbonate, water, brine
  10. dry with materialdried (MgSO4)
  11. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-778e8b2c7a094def9af9712c89d43229
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576339

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