HCID 19856012, compound → HCID 135745116, compound

HRID 2073761Notes

Reaction equation

HRID 2073761 reaction equation
[NH2:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH3:17])[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.CN1CCCC1=O.O>[CH2:16]([C:12]1[CH:11]=[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:15]=[CH:14][CH:13]=1)[CH3:17]

Participants

7

Reactant 2

HCID 19856012HCID 19856012, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135745116HCID 135745116, compoundYield 77.2%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

496 mg of 4-amino-3-(3-ethylphenyl)-5-isothiazolecarboxamide in 7 ml of glacial acetic acid, 4 ml of concentrated hydrochloric acid and 4 ml of N-methyl-pyrrolidone was stirred at 0° C. during the addition of 165 mg of sodium nitrite in 1 ml of water. The mixture was held at 0° C. for 1.5 hours then filtered and the solid residue was recrystallized from ethanol to give 400 mg of 7-(3-ethylphenyl)isothiazolo[4,5-d]-1,2,3-triazin-4(3H)-one, m.p. 156°-157° C. (dec.).

Workup

  1. filtrationthen filtered
  2. customthe solid residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-4772f0a74f1c4e59b588c3db1096e9ff
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

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