Nitric Acid → 2,4-Dichloro-5-nitro-1,3-thiazole

HRID 255579Notes

Reaction equation

HRID 255579 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[C:5]([Cl:7])[N:6]=1.[N+:8]([O-])([OH:10])=[O:9]>>[Cl:1][C:2]1[S:3][C:4]([N+:8]([O-:10])=[O:9])=[C:5]([Cl:7])[N:6]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 123331552,4-Dichlorothiazole

Product 1

HCID 138518172,4-Dichloro-5-nitro-1,3-thiazoleYield 95.5%

Procedure

400 g (2.6 mols) of 2,4-dichloro-thiazole are introduced in portions, in the course of one hour at between 15° and 20° C., into 2 liters of 98% strength nitric acid (density=1.51; about 47 mols), while stirring and cooling. Thereafter, the mixture is discharged in portions onto about 20 kg of ice/water, while stirring thoroughly and the precipitate formed is filtered off under suction while still cold, washed neutral with water and dried between clay plates. 494 g (95.5% of theory) of 2,4-dichloro-5-nitro-thiazole are obtained in this manner. Melting point of a sample recrystallized from low-boiling petroleum ether: 38°-39° C.

Workup

  1. temperaturecooling
  2. stirringwhile stirring thoroughly
  3. customthe precipitate formed
  4. filtrationis filtered off under suction while still cold,
  5. washwashed neutral with water
  6. customdried between clay plates

Sources & evidence

ORD record
ord-7a1a54c8f36c439785a3a15904bad28f
Source dataset
uspto-grants-1987_10
Patent number
US04698357

Reaction notes

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