Hydrochloric Acid → 1,4-Cyclohexadiene-1,4-dicarboxylic acid, 2,5-bis[(4-methylphenyl)amino]-, 1,4-dimethyl ester

HRID 2056972

반응식

HRID 2056972 반응식
[CH3:1][O:2][C:3]([CH:5]1[C:11](=O)[CH2:10][CH:9]([C:13]([O:15][CH3:16])=[O:14])[C:7](=O)[CH2:6]1)=[O:4].[CH3:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.Cl>CO>[CH3:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:7]2[CH2:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:11]([NH:22][C:21]3[CH:23]=[CH:24][C:18]([CH3:17])=[CH:19][CH:20]=3)[CH2:10][C:9]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:20][CH:19]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 948661,4-Cyclohexanedicarboxylic acid, 2,5-dioxo-, 1,4-dimethyl ester

생성물 1

HCID 1171141,4-Cyclohexadiene-1,4-dicarboxylic acid, 2,5-bis[(4-methylphenyl)amino]-, 1,4-dimethyl ester수율 97.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Dimethyl 1,4-cyclohexanedione-2,5-dicarboxylate (4.56 gm; 20 mmol) and methanol (100 ml) were heated to boiling; then 4-methylaniline (4.5 gm; 42 mmol) was added followed by conc. hydrochloric acid (200 μl). The mixture was refluxed for 5 hours under a nitrogen atmosphere. On cooling a cream solid precipitated out which was collected by filtration, washed with methanol and dried under vacuum to give 7.92 gm (97%) of dimethyl 2,5-bis{(4-methylphenyl)amino}cyclohexa-1,4-diene-1,4-dicarboxylate.

후처리

  1. temperatureThe mixture was refluxed for 5 hours under a nitrogen atmosphere
  2. temperatureOn cooling a cream solid
  3. customprecipitated out which
  4. filtrationwas collected by filtration
  5. washwashed with methanol
  6. customdried under vacuum

출처 및 근거

ORD 기록
ord-5abab54315e844ccb7e5e7f3a42cf97a
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335771B2

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