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Ammonium Chloride → 2-bromo-N-(2,4,6-trimethoxyphenyl)decanamide

HRID 2379601
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HRID 2379601 반응식
[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([OH:5])=O.[CH3:14][O:15][C:16]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[C:17]=1[NH2:18].[Cl-].[NH4+]>S(Cl)(Cl)=O.N1C=CC=CC=1>[Br:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:3]([NH:18][C:17]1[C:19]([O:25][CH3:26])=[CH:20][C:21]([O:23][CH3:24])=[CH:22][C:16]=1[O:15][CH3:14])=[O:5]
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참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 842712,4,6-TrimethoxyanilineHCID 983102-Bromodecanoic acid

생성물 1

HCID 149953882-bromo-N-(2,4,6-trimethoxyphenyl)decanamide수율 69.5%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 24386Thionyl Chloride
용매

실험 절차

2-Bromodecanoic acid (1 g, 3.8 mmol) was heated under reflux in thionyl chloride (10 ml) for 1 hour. The thionyl chloride was evaporated and the residue was dissolved in dry ether (10 ml) and added dropwise to a solution of 2,4,6-trimethoxyaniline (0.7 g, 3.8 mmol) in pyridine (20 ml) at 0° C. and the mixture was stirred for 1.5 hours. The reaction mixture was poured into saturated aqueous ammonium chloride and extracted three times with ethyl acetate (60 ml). The combined organics were extracted with water and brine and dried and concentrated. Recrystallization from isopropyl ether afforded 1.1 g (65%) of the title compound, m.p. 109°-110° C. This material was used directly in the next step.

후처리

  1. customThe thionyl chloride was evaporated
  2. dissolutionthe residue was dissolved in dry ether (10 ml)
  3. extractionextracted three times with ethyl acetate (60 ml)
  4. extractionThe combined organics were extracted with water and brine
  5. customdried
  6. concentrationconcentrated
  7. customRecrystallization from isopropyl ether

출처 및 근거

ORD 기록
ord-a039717299314874b89da6ba08f56f92
출처 데이터셋
uspto-grants-1994_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05362878

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