2,4-Dinitrobenzoic acid → (2,4-Dinitrophenyl)(4-methylpiperazin-1-yl)methanone

HRID 2108144

반응식

HRID 2108144 반응식
[N+:1]([C:4]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH3:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.P(Cl)(Cl)(Cl)=O.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:19][CH2:18]1

참가 물질

7

반응물 4

HCID 118802,4-Dinitrobenzoic acidHCID 24813Phosphorus oxychlorideHCID 531671-MethylpiperazineHCID 516892Sodium Bicarbonate

생성물 1

HCID 4090619(2,4-Dinitrophenyl)(4-methylpiperazin-1-yl)methanone수율 54.7%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8471Triethylamine용매

반응 조건

온도
80 °C

실험 절차

To a slurry of 212.0 g of 2,4-dinitrobenzoic acid in 1400 ml of toluene was added with agitation 101.0 g of triethylamine, followed by 122.7 g of N-methylpiperazine. Next 75.7 g of phosphorus oxychloride was added dropwise at such a rate to maintain the reaction temperature below 90° C. The mixture was refluxed for 5 hrs. cooled to 80° C., and poured slowly into 1000 ml of aqueous 5% NaHCO3 solution with stirring. The precipitate was filtered, washed with water and recrystallized from hot methanol to yield 161 g of N1 -methyl-N4 -(2,4-dinitrobenzoyl)- piperazine, mp 130°-132° C.

후처리

  1. temperatureto maintain the reaction temperature below 90° C
  2. temperatureThe mixture was refluxed for 5 hrs
  3. filtrationThe precipitate was filtered
  4. washwashed with water
  5. customrecrystallized from hot methanol

출처 및 근거

ORD 기록
ord-648c22ff6e9d47bf80ef0ac41f1f532f
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04937306

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