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Formic Acid → Iguratimod

HRID 1031697
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HRID 1031697 반응식
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[C:17](=[O:18])[C:16]2[CH:19]=[C:20]([O:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][C:15]=2[O:14][CH:13]=1.C(OC(C)C)(C)C>C(Cl)Cl>[CH:1]([NH:11][C:12]1[C:17](=[O:18])[C:16]2[CH:19]=[C:20]([O:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:21]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:22][C:15]=2[O:14][CH:13]=1)=[O:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 284Formic AcidHCID 7914Diisopropyl EtherHCID 7918Acetic AnhydrideHCID 10783765HCID 10783765, 화합물

생성물 1

HCID 124246Iguratimod수율 73%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

27.6 g of formic acid was added to 30.6 g of acetic anhydride. The mixture was stirred for 1.5 hours at 40°-45° C. The reaction mixture was dropwise added to a solution of 34.6 g of 3-amino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one dissolved in 400 ml of methylene chloride. The mixture was stirred for 1 hour at 20°-25° C. 400 ml of diisopropyl ether was added thereto. The resulting crystal was collected by filtration and recrystallized from acetonitrile to obtain 27.3 g (yield: 73%) of 3-formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of 236°-238° C.

후처리

  1. stirringThe mixture was stirred for 1 hour at 20°-25° C
  2. filtrationThe resulting crystal was collected by filtration
  3. customrecrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-315b412ca86144f5a85423bf0924ffc6
출처 데이터셋
uspto-grants-1990_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04954518

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