Aniline → 2-Anilino-4-chloro-5-nitrothiazole

HRID 1461367Notes

Reaction equation

HRID 1461367 reaction equation
C(=O)(O)[O-].[Na+].Cl[C:7]1[S:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([Cl:12])[N:11]=1.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[NH:16]([C:7]1[S:8][C:9]([N+:13]([O-:15])=[O:14])=[C:10]([Cl:12])[N:11]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 138518172,4-Dichloro-5-nitro-1,3-thiazole

Product 1

HCID 150589182-Anilino-4-chloro-5-nitrothiazoleYield 94.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

252 g (3.0 mols) of sodium bicarbonate are added to a solution of 360 g (1.8 mols) of 2,4-dichloro-5-nitrothiazole in 1.5 l of acetonitrile. A mixture of 139.5 g (1.5 mols) of aniline and 1,500 ml of acetonitrile is then added dropwise at -10° C. to -15° C. in the course of about 4.5 hours and the mixture is subsequently stirred at the same temperature for a further 4 hours. It is then stirred into 15 l of ice-water and the precipitate is filtered off, washed with water and dried. To remove excess 2,4-dichloro-5-nitrothiazole, the product is stirred into 2.4 l of petroleum ether at room temperature, filtered off, washed with petroleum ether and dried. 361.7 g (94.4% of theory) of 2-anilino-4-chloro-5-nitrothiazole of melting point 186° C. to 187° C. (decomposition) are obtained.

Workup

  1. additionis then added dropwise at -10° C. to -15° C. in the course of about 4.5 hours
  2. filtrationthe precipitate is filtered off
  3. washwashed with water
  4. customdried
  5. customTo remove excess 2,4-dichloro-5-nitrothiazole
  6. stirringthe product is stirred into 2.4 l of petroleum ether at room temperature
  7. filtrationfiltered off
  8. washwashed with petroleum ether
  9. customdried

Sources & evidence

ORD record
ord-c533bd4e6cb14d8aa83c8a3d93dd7d24
Source dataset
uspto-grants-1991_12
Patent number
US05075326

Reaction notes

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