Ethyl Acetate → HCID 22728032, compound

HRID 2300404Notes

Reaction equation

HRID 2300404 reaction equation
[N+:1]([C:4]1[C:5](N)=[C:6]([Cl:13])[C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-:3])=[O:2].N(OS(=O)(=O)O)=O.O[PH2]=O.CCOC(C)=O>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:5]=[C:6]([Cl:13])[C:7]2[S:11][CH:10]=[N:9][C:8]=2[CH:12]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 82157Nitrosylsulfuric acidHCID 4124402Phosphinic AcidHCID 227280267-Chloro-5-nitro-6-benzothiazolamine

Product 1

HCID 22728032HCID 22728032, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-nitro-6-amino-7-chlorobenzothiazole (0.21 g, 0.91 mmol) in 4 mL of sulfuric acid was added nitrososulfuric acid (0.20 g, 1.6 mmol) in a portion. The resulting reaction mixture was stirred for 12 h at 25° C. It was then cooled to 0° C. and 0.3 mL of H3PO2 was added into the mixture. Reaction mixture was stirred for another 12 h at 25° C. and for 2 h at 50° C., poured into EtOAc and washed with aq. NaHCO3. Organic layer was dried over Na2SO4 and concentrated in vacuo to provide an oil, which was purified on column chromatography (EtOAc, neat) to produce the desired product (0.12 g, 0.56 mmol, 62%).

Workup

  1. customThe resulting reaction mixture
  2. temperatureIt was then cooled to 0° C.
  3. customReaction mixture
  4. stirringwas stirred for another 12 h at 25° C. and for 2 h at 50° C.
  5. washwashed with aq. NaHCO3
  6. dry with materialOrganic layer was dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customto provide an oil, which
  9. customwas purified on column chromatography (EtOAc, neat)

Sources & evidence

ORD record
ord-628828416b4d446c950d5b9755e22411
Source dataset
uspto-grants-2002_12
Patent number
US06498177B2

Reaction notes

Loading…