Ammonium Carbonate → 4-Chloro-5-nitro-1,3-thiazol-2-ylamine

HRID 1461368Notes

Reaction equation

HRID 1461368 reaction equation
C(=O)([O-])[O-].[NH4+:5].[NH4+].Cl[C:8]1[S:9][C:10]([N+:14]([O-:16])=[O:15])=[C:11]([Cl:13])[N:12]=1>C(#N)C>[NH2:5][C:8]1[S:9][C:10]([N+:14]([O-:16])=[O:15])=[C:11]([Cl:13])[N:12]=1

Participants

4

Reactant 2

HCID 517111Ammonium CarbonateHCID 138518172,4-Dichloro-5-nitro-1,3-thiazole

Product 1

HCID 150589194-Chloro-5-nitro-1,3-thiazol-2-ylamineYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10.1 g (0.105 mol) of ammonium carbonate are added to a solution of 19.9 g (0.1 mol) of 2,4-dichloro-5-nitrothiazole in 200 ml of acetonitrile, while stirring, and stirring is continued at room temperature for two days. The mixture is then stirred into 1 l of ice-water and the precipitate is filtered off, washed with water and dried. To remove unreacted 2,4-dichloro-5-nitrothiazole, the product is stirred into about 100 ml of petroleum ether at room temperature, filtered off, washed with petroleum ether and dried. 12.2 g (68.0% of theory) of 2-amino-4-chloro-5-nitrothiazole of melting point 180° C. (decomposition) are obtained.

Workup

  1. stirringstirring
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customdried
  5. customTo remove unreacted 2,4-dichloro-5-nitrothiazole
  6. stirringthe product is stirred into about 100 ml of petroleum ether at room temperature
  7. filtrationfiltered off
  8. washwashed with petroleum ether
  9. customdried

Sources & evidence

ORD record
ord-cdff517840a849afb1f0d2186b0b53d4
Source dataset
uspto-grants-1991_12
Patent number
US05075326

Reaction notes

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