Sodium Chloride → N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide

HRID 2214533

반응식

HRID 2214533 반응식
[CH3:1][C:2]1([CH3:12])[O:6][C:5](=[CH:7][C:8]([OH:10])=O)[C:4](=[O:11])[O:3]1.C(Cl)(=O)C(Cl)=O.Cl.[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:24][NH:25][CH3:26].[Cl-].[Na+]>C1C=CC=CC=1.C(Cl)Cl.N1C=CC=CC=1.Cl>[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:24][N:25]([CH3:26])[C:8](=[O:10])[CH:7]=[C:5]1[C:4](=[O:11])[O:3][C:2]([CH3:1])([CH3:12])[O:6]1

참가 물질

9

반응물 4

HCID 5234Sodium ChlorideHCID 65578Oxalyl chlorideHCID 172938771-(3,4-Dichlorophenyl)-N-methylmethanamine hydrochlorideHCID 68860642(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetic acid

생성물 1

HCID 69655735N-(3,4-Dichloro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methyl-acetamide수율 82%

시약·촉매·용매 4

HCID 241Benzene용매HCID 313Hydrochloric Acid용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a suspension of (2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-acetic acid, Compound III-A, (4.5 g, 26.2 mmol) in benzene (30 mL) was added oxalyl chloride (15 mL) and the resulting mixture was heated at reflux for 1 h. The mixture was cooled to room temp. and concentrated. The residue was dissolved in methylene chloride (30 mL) and cooled to 0° C. To this was added a suspension of (3,4-dichloro-benzyl)-methyl-amine hydrochloride salt (5.0 g, 22.1 mmol) in methylene chloride (30 mL) and pyridine (18 mL). The resulting mixture was stirred at room temp for 18 h then diluted with 1N HCl. The aqueous phase was saturated with sodium chloride and extracted with methylene chloride (3 times). The organic layers were combined, dried (Na2SO4), and concentrated. The brown oil was purified over silica gel eluting with ethyl acetate/hexane (1:1) to give the title compound as a pale yellow oil that solidified to a white solid upon standing (6.2 g, 82% yield). 1H NMR (300 MHz, DMSO) δ: 7.44–7.10 (m, 3H), 6.16 (s, 0.66H), 6.08 (s, 0.33H), 4.59 (s, 1.33H), 4.53 (s, 0.67H), 3.02 (s, 2H), 2.97 (s, 1H), 1.74 (s, 4H), 1.69 (s, 2H).

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureThe mixture was cooled to room temp.
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in methylene chloride (30 mL)
  6. additionTo this was added
  7. extractionextracted with methylene chloride (3 times)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe brown oil was purified over silica gel eluting with ethyl acetate/hexane (1:1)

출처 및 근거

ORD 기록
ord-ca545db157cc491aace4a2e01517f5f2
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07109186B2

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