Dimethylformamide → HCID 135745138, compound

HRID 2073764Notes

Reaction equation

HRID 2073764 reaction equation
C(OC1C=[CH:9][C:8]([C:11]2[C:15]3[N:16]=[N:17][NH:18][C:19](=[O:20])[C:14]=3[S:13][N:12]=2)=[CH:7][C:6]=1[C:21]#[N:22])C=C.C[N+]1([O-])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.S(S([O-])=O)([O-])=[O:32].[Na+].[Na+].CN(C)[CH:41]=[O:42]>O.[Os](=O)(=O)(=O)=O>[C:21]([C:6]1[CH:7]=[C:8]([C:11]2[C:15]3[N:16]=[N:17][NH:18][C:19](=[O:20])[C:14]=3[S:13][N:12]=2)[CH:9]=[CH:29][C:28]=1[O:27][CH2:26][CH:25]([OH:32])[CH2:41][OH:42])#[N:22]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24489Sodium DithioniteHCID 82029Methyl morpholine oxideHCID 135745112HCID 135745112, compound

Product 1

HCID 135745138HCID 135745138, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent3×

Procedure

A solution of 500 mg of 7-(4-allyloxy-3-cyanophenyl)isothiazolo[4,5-d]-1,2,3-triazin-4(3H)-one and 200 mg of N-methylmorpholine N-oxide in 15 ml of dimethylformamide and 5 ml of water was treated with 1.75 ml of a 0.4% solution of osmium tetroxide in water. The mixture was stirred at room temperature for 7 days and then a solution of 220 mg of sodium dithionite in 5 ml of water was added. The solvent was removed by evaporation and the residue was extracted with hot ethyl acetate, filtered and the filtrate was evaporated. Recrystallization of the residue from acetic acid yielded 160 mg of 7-[3-cyano-4-(2,3-dihydroxypropoxy)phenyl]isothiazolo[4,5-d]-1,2,3-triazin-4(3H)-one as a white solid of melting point 195° C. (dec.).

Workup

  1. customThe solvent was removed by evaporation
  2. extractionthe residue was extracted with hot ethyl acetate
  3. filtrationfiltered
  4. customthe filtrate was evaporated
  5. customRecrystallization of the residue from acetic acid

Sources & evidence

ORD record
ord-a6533e3c233841609a198d0b58e8eb40
Source dataset
uspto-grants-1990_04
Patent number
US04920119

Reaction notes

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