Sodium Nitrite → HCID 136114008, compound

HRID 2073763Notes

Reaction equation

HRID 2073763 reaction equation
[NH2:1][C:2]1[C:3]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[CH:12][CH:11]=2)=[N:4][S:5][C:6]=1[C:7]([NH2:9])=[O:8].[N:27]([O-])=O.[Na+]>Cl.CN1CCCC1=O.O>[CH2:20]([O:19][C:17]([NH:16][C:13]1[CH:12]=[CH:11][C:10]([C:3]2[C:2]3[N:1]=[N:27][NH:9][C:7](=[O:8])[C:6]=3[S:5][N:4]=2)=[CH:15][CH:14]=1)=[O:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 23668193Sodium NitriteHCID 54356052HCID 54356052, compound

Product 1

HCID 136114008HCID 136114008, compoundYield 71.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

22.5 g of 4-amino-3-(4-benzyloxyformamidophenyl)-5-isothiazolecarboxamide in 25 ml of concentrated hydrochloric acid and 150 ml of N-methylpyrrolidone were cooled in an ice-bath and stirred during the addition of 4.89 g of sodium nitrite dissolved in 20 ml of water. After 0.5 hour 150 ml of water were added and the resulting precipitate was filtered off, washed with water, dried in vacuo and recrystallized from ethyl acetate to yield 16.6 g of 7-(4-benzyloxyformamidophenyl)isothiazolo[4,5-d]-1,2,3-triazin-4(3H)-one of melting point 190°-191° C. (dec.).

Workup

  1. filtrationthe resulting precipitate was filtered off
  2. washwashed with water
  3. customdried in vacuo
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-d71529645b404a859e2f2e47050b433d
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

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