Phenol → 4-Chloro-5-nitro-2-phenoxythiazole

HRID 1461365Notes

Reaction equation

HRID 1461365 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.[C:17]1([OH:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[Cl:13][C:11]1[N:12]=[C:8]([O:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[S:9][C:10]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 138518172,4-Dichloro-5-nitro-1,3-thiazole

Product 1

HCID 199805594-Chloro-5-nitro-2-phenoxythiazoleYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

42 g (0.036 mol) of anhydrous potassium carbonate are added to a solution of 72.0 g (0.36 mol) of 2,4-dichloro-5-nitrothiazole in 300 ml of acetonitrile. A solution of 28.2 g (0.3 mol) of phenol in 300 ml of acetonitrile is then added dropwise at 15° C. to 20° C. in the course of about 1.5 hours and the mixture is subsequently stirred at the same temperature for a further 0.5 hour. It is then heated at the reflux temperature for 15 minutes, cooled to room temperature and then stirred into 3 liters 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 500 ml of petroleum ether at about 20° C., filtered off, washed with petroleum ether and dried. 75.4 g (98.0% of theory) of 4-chloro-5-nitro-2-phenoxythiazole are thus obtained. Melting point 96° C. (from petroleum ether).

Workup

  1. temperatureIt is then heated at the reflux temperature for 15 minutes
  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 in 500 ml of petroleum ether at about 20° C.
  7. filtrationfiltered off
  8. washwashed with petroleum ether
  9. customdried

Sources & evidence

ORD record
ord-01e73d9521f9431f9ba54fa5967f16f0
Source dataset
uspto-grants-1991_12
Patent number
US05075326

Reaction notes

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