4,5-Dichlorophthalic anhydride → 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide

HRID 225461

반응식

HRID 225461 반응식
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=[O:8].[Cl:10][C:11]1[CH:12]=[C:13]2[C:18](=O)[O:17][C:15](=[O:16])[C:14]2=[CH:20][C:21]=1[Cl:22]>C(O)(=O)C>[Cl:10][C:11]1[CH:12]=[C:13]2[C:14](=[CH:20][C:21]=1[Cl:22])[C:15](=[O:16])[N:1]([C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([NH2:9])=[O:8])[C:18]2=[O:17]

참가 물질

4

반응물 2

HCID 703344,5-Dichlorophthalic anhydrideHCID 5189933-Aminothiophene-2-carboxamide

생성물 1

HCID 690749393-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

3-aminothiophene-2-carboxamide was added to an acetic acid solution of 4,5-dichlorophthalic anhydride and stirred all night heated to reflux to give 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide. 1M NaOH aq was added to THF-MeOH solution of the obtained 3-(5,6-dichloro-1,3-dioxo-1,3-dihydro-2H-isoindole-2-yl)thiophene-2-carboxamide and stirred for 2.5 hours at 80° C. to give 4,5-dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoic acid. Sulfuric acid was added to a MeOH-1,4-dioxane solution of the obtained 4,5-dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoic acid and stirred for three days at 70° C. to give methyl 4,5-dichloro-2-(4-oxo-3,4-dihydrothieno[3,2-d]pyrimidine-2-yl)benzoate.

후처리

  1. temperatureheated
  2. temperatureto reflux

출처 및 근거

ORD 기록
ord-8036fccdbecc4c7b9099ebc740f635a3
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557112B2

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