HCID 19856004, compound → HCID 135745140, compound

HRID 2073762Notes

Reaction equation

HRID 2073762 reaction equation
[NH2:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[N:4][S:5][C:6]=1[C:7]([NH2:9])=[O:8].[N:18]([O-])=O.[Na+]>C(O)(=O)C.Cl.O>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[C:2]3[N:1]=[N:18][NH:9][C:7](=[O:8])[C:6]=3[S:5][N:4]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 2

HCID 19856004HCID 19856004, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135745140HCID 135745140, compoundYield 78.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

1 g of 4-amino-3-(4-methoxyphenyl)-5-isothiazolecarboxamide in 10 ml of glacial acetic acid and 3 ml of concentrated hydrochloric acid was stirred at 0° C. during the addition of a solution of 416 mg of sodium nitrite in 5 ml of water. The cooling bath was removed, the mixture was stirred for 1 hour and the precipitated product was removed by filtration. Recrystallization from aqueous dimethylformamide gave 820 mg of 7-(4-methoxyphenyl)-isothiazolo[4,5-d]-1,2,3-triazin-4(3H)-one as an off-white solid of melting point 213° C. (dec.).

Workup

  1. customThe cooling bath was removed
  2. customthe precipitated product was removed by filtration
  3. customRecrystallization from aqueous dimethylformamide

Sources & evidence

ORD record
ord-f1d7ce8677c64581a018f9f2f4fdc81a
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

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