3-Bromoaniline → 2-(3-Bromophenylamino)-4-chloro-5-nitrothiazole

HRID 1088210Notes

Reaction equation

HRID 1088210 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10]1[S:11][C:12]([N+:16]([O-:18])=[O:17])=[C:13]([Cl:15])[N:14]=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:10]2[S:11][C:12]([N+:16]([O-:18])=[O:17])=[C:13]([Cl:15])[N:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 138518172,4-Dichloro-5-nitro-1,3-thiazole

Product 1

HCID 150589172-(3-Bromophenylamino)-4-chloro-5-nitrothiazoleYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 8.6 g (0.05 mol) of 3-bromoaniline in 100 ml of dimethylformamide is added dropwise to a solution of 12.0 g (0.06 mol) of 2,4-dichloro-5-nitrothiazole in 100 ml of dimethylformamide at 0° C. to 5° C. in the course of about 2 hours and the mixture is subsequently stirred at the same temperature for a further 4 hours. It is then stirred into 1,000 ml 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 in 80 ml of petroleum ether at room temperature, filtered off, washed with petroleum ether and dried. 16.0 g (95.7% of theory) of 2-(3-bromophenylamino)-4-chloro-5-nitrothiazole of melting point 191° C. to 192° C. (decomposition) are thus obtained.

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed with water
  3. customdried
  4. customTo remove excess 2,4-dichloro-5-nitrothiazole
  5. stirringthe product is stirred in 80 ml of petroleum ether at room temperature
  6. filtrationfiltered off
  7. washwashed with petroleum ether
  8. customdried

Sources & evidence

ORD record
ord-207f470a102b452e9918a51748b93b85
Source dataset
uspto-grants-1990_10
Patent number
US04962102

Reaction notes

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