Formic Acid → Iguratimod

HRID 1031697Notes

Reaction equation

HRID 1031697 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 124246IguratimodYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-315b412ca86144f5a85423bf0924ffc6
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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