Water → 2-amino-3-carbamoyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

HRID 1031740Notes

Reaction equation

HRID 1031740 reaction equation
[C:1]([C:3]1[C:8](=[O:9])[C:7]2[CH:10]=[C:11]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]([NH:14][S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][C:6]=2OC=1)#[N:2].Cl.N[OH:28].O.C[N:31](C)[CH:32]=[O:33]>C(O)C>[NH2:31][C:32]1[O:33][C:6]2[CH:13]=[C:12]([NH:14][S:15]([CH3:18])(=[O:16])=[O:17])[C:11]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:10][C:7]=2[C:8](=[O:9])[C:3]=1[C:1](=[O:28])[NH2:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 443297Hydroxyamine hydrochlorideHCID 147224153-cyano-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

Product 1

HCID 147224242-amino-3-carbamoyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-oneYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.56 g of 3-cyano-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one, 970 mg of hydroxylamine hydrochloride, 1.5 ml of water, 7 ml of N,N-dimethylformamide and 150 ml of ethanol were mixed, and subjected to refluxing for 3 hours. The reaction mixture was cooled, and thereafter, the precipitated crystals were collected by filtration and then recrystallized from acetonitrile to obtain 2.8 g (yield: 72%) of 2-amino-3-carbamoyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of >250° C.

Workup

  1. temperatureto refluxing for 3 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe precipitated crystals were collected by filtration
  4. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-5a7fca6c37fb496e93e1186aa3525605
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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