Methyl 4-chloroformylbutyrate → 4-[(2,4-Dinitro-phenyl)-methyl-carbamoyl]-butyric acid methyl ester

HRID 1967482노트

반응식

HRID 1967482 반응식
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH3:15][O:16][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>>[CH3:15][O:16][C:17](=[O:24])[CH2:18][CH2:19][CH2:20][C:21](=[O:22])[N:2]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13])[CH3:1]

참가 물질

3

반응물 2

HCID 73916Methyl 4-chloroformylbutyrateHCID 74891N-methyl-2,4-dinitroaniline

생성물 1

HCID 583828074-[(2,4-Dinitro-phenyl)-methyl-carbamoyl]-butyric acid methyl ester수율 79%

반응 조건

온도
138 °C

실험 절차

To a stirred suspension of 1-methylamino-2,4-dinitrobenzene (1.00 g, 5.07 mmol) in xylenes (10 mL) was added methyl-5-chloro-5-oxo-valerate (3.50 mL, 25.28 mmol, 5.0 equiv.) at 20° C. The reaction mixture was then heated to reflux, approximately 138° C. Reaction progress was monitored periodically by HPLC Method A. The reaction was complete after stirring for approximately 24 hours at 138° C. The reaction mixture was cooled to 0° C. and hexanes was added (10 mL) to crystallize the product. The resultant slurry was stirred for approximately 1 hour at −10° C. to 0° C. and then filtered. The wet cake was dried at 60° C. under vacuum/N2 sweep overnight to give 1.30 g (79% yield) as an off-while solid.

후처리

  1. temperatureThe reaction mixture was then heated
  2. customReaction progress
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customto crystallize the product
  5. stirringThe resultant slurry was stirred for approximately 1 hour at −10° C. to 0° C.
  6. filtrationfiltered
  7. dry with materialThe wet cake was dried at 60° C. under vacuum/N2
  8. waitsweep overnight
  9. customto give 1.30 g (79% yield) as an off-while solid

출처 및 근거

ORD 기록
ord-749aac15b78248ce9e5ca48ac48c6c1c
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420829B2

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