Dimethyl acetylenedicarboxylate → HCID 178418430, 화합물

HRID 3105

반응식

HRID 3105 반응식
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]([Cl:13])[C:3]=1[C:4]([O:6]C)=O.[C:14]([C:20]([O:22][CH3:23])=[O:21])#[C:15][C:16]([O:18][CH3:19])=[O:17].CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Cl:13][C:8]1[CH:9]=[C:10]([Cl:12])[CH:11]=[C:2]2[C:3]=1[C:4]([OH:6])=[C:14]([C:20]([O:22][CH3:23])=[O:21])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[N:1]2

참가 물질

5

반응물 3

HCID 12980Dimethyl acetylenedicarboxylateHCID 12363232Methyl 2-amino-4,6-dichlorobenzoateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 178418430HCID 178418430, 화합물수율 59%

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

A solution of methyl 2-amino-4,6-dichlorobenzoate (1.30 g, 5.91 mM) and dimethyl acetylenedicarboxylate (0.96 g, 6.78 mM) in t-butanol (14 mL) was refluxed for 18 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and potassium t-butoxide (0.76 g, 6.8 mM) was added to the stirred mixture whereupon a precipitate formed. After refluxing for 1.5 hr, the reaction mixture was cooled to room temperature and filtered to separate the precipitated solids. The solids were washed with t-butanol and then dissolved in water. The resulting solution was acidified with 1N H2SO4 and the resulting precipitate was collected, washed thoroughly with water and dried to give the title compound as a light green solid (1.15 g, 59%). An analytical sample was obtained by recrystallization of a portion from toluene to provide the title compound as a light tan solid, mp 109.5°-111° C. (d); MS(CI): 330 (M+H).

후처리

  1. customformed
  2. temperatureAfter refluxing for 1.5 hr
  3. temperaturethe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. customto separate the precipitated solids
  6. washThe solids were washed with t-butanol
  7. dissolutiondissolved in water
  8. customthe resulting precipitate was collected
  9. washwashed thoroughly with water
  10. customdried

출처 및 근거

ORD 기록
ord-80b7e4ba59954100866003a993d7b735
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733910

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