Ammonia → 3-carbamoyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one

HRID 1031705Notes

Reaction equation

HRID 1031705 reaction equation
[C:1]([C:4]1[C:9](=[O:10])[C:8]2[CH:11]=[C:12]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][C:7]=2[O:6][CH:5]=1)(O)=[O:2].P(Cl)(Cl)(Cl)=O.[NH3:32].Cl>CN(C)C=O>[C:1]([C:4]1[C:9](=[O:10])[C:8]2[CH:11]=[C:12]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:13]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:14][C:7]=2[O:6][CH:5]=1)(=[O:2])[NH2:32]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 24813Phosphorus oxychlorideHCID 108094623-carboxy-7-methylsulfonylamino-6-phenoxy4H-1-benzopyran-4-one

Product 1

HCID 107855963-carbamoyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-oneYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.75 g of 3-carboxy-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one was suspended in 75 ml of N,N-dimethylformamide. Thereto was dropwise added 4.6 g of phosphorus oxychloride at -10° to -5° C. The mixture was stirred for 3 hours at the same temperature. The reaction mixture was dropwise added to 40 ml of a concentrated aqueous ammonia solution at 10°-20° C. The mixture was stirred for 30 minutes at the same temperature and then adjusted to pH 4 with 4N hydrochloric acid. The resulting crystal was collected by filtration, washed with water and recrystallized from acetic acid to obtain 2.81 g (yield: 75.1%) of 3-carbamoyl-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one having a melting point of >250° C.

Workup

  1. customat -10° to -5° C
  2. stirringThe mixture was stirred for 30 minutes at the same temperature
  3. filtrationThe resulting crystal was collected by filtration
  4. washwashed with water
  5. customrecrystallized from acetic acid

Sources & evidence

ORD record
ord-eda1c87faaff4d269edff735f7acf2ac
Source dataset
uspto-grants-1990_09
Patent number
US04954518

Reaction notes

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