Benzylamine → 2-Benzylamino-4-chloro-5-nitrothiazole

HRID 1461370Notes

Reaction equation

HRID 1461370 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[S:9][C:10]([N+:14]([O-:16])=[O:15])=[C:11]([Cl:13])[N:12]=1.[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C>[CH2:17]([NH:24][C:8]1[S:9][C:10]([N+:14]([O-:16])=[O:15])=[C:11]([Cl:13])[N:12]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 138518172,4-Dichloro-5-nitro-1,3-thiazole

Product 1

HCID 150589202-Benzylamino-4-chloro-5-nitrothiazoleYield 95.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

7.0 g (0.051 mol) of anhydrous potassium carbonate are added to a solution of 12.0 g (0.06 mol) of 2,4-dichloro-5-nitrothiazole in 50 ml of acetonitrile. A mixture of 5.35 g (0.05 mol) of benzylamine and 50 ml of acetonitrile is then added dropwise at 15° C. to 20° C. in the course of about half an hour and the mixture is subsequently stirred at room temperature for a further hour. It is then heated at the reflux temperature for 15 minutes, cooled to room temperature and stirred into about 500 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 into 80 ml of petroleum ether at room temperature, filtered off, washed with petroleum ether and dried. 12.9 g (95.7% of theory) of 2-benzylamino-4-chloro-5-nitrothiazole of melting point 195° C. to 196° C. (decomposition) are obtained.

Workup

  1. additionis then added dropwise at 15° C. to 20° C. in the course of about half an hour
  2. temperatureIt is then heated at the reflux temperature for 15 minutes
  3. temperaturecooled to room temperature
  4. filtrationthe precipitate is filtered off
  5. washwashed with water
  6. customdried
  7. customTo remove excess 2,4-dichloro-5-nitrothiazole
  8. stirringthe product is stirred into 80 ml of petroleum ether at room temperature
  9. filtrationfiltered off
  10. washwashed with petroleum ether
  11. customdried

Sources & evidence

ORD record
ord-2a25bd91b92545239ca9a164acd50f0c
Source dataset
uspto-grants-1991_12
Patent number
US05075326

Reaction notes

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