Hydrochloric Acid → 2-Chloro-4-methyl-5-(4-nitro-phenyl)-thiazole

HRID 908154Notes

Reaction equation

HRID 908154 reaction equation
N(OCCC(C)C)=O.[CH3:9][C:10]1[N:11]=[C:12](N)[S:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.[ClH:25]>CC#N.[Cu](Cl)Cl>[Cl:25][C:12]1[S:13][C:14]([C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)=[C:10]([CH3:9])[N:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 6166034-Methyl-5-(p-nitrophenyl)-2-thiazolamine

Product 1

HCID 673914002-Chloro-4-methyl-5-(4-nitro-phenyl)-thiazole

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Isoamyl nitrite (3.5 ml, 25 mmol) is added to a stirred suspension/solution of anhydrous copper (II) chloride (2.75 g, 20 mmol) in dry methylcyanide (50 ml). 4-Methyl-5-(4-nitro-phenyl)-thiazol-2-ylamine (25a) (4.0 g, 17 mmol) is then added over 30 minutes. The resulting slurry is stirred at room temperature for 1 hour then heated at 70° C. for 30 minutes. After cooling to room temperature the black solution is poured into 4M hydrochloric acid (200 ml). The product is extracted with ethyl acetate, dried (MgSO4) and the solvent removed to give the title compound as an orange powder (3.13 g). MH+ (TOF, ES+): 255.0

Workup

  1. temperaturethen heated at 70° C. for 30 minutes
  2. temperatureAfter cooling to room temperature the black solution
  3. extractionThe product is extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed

Sources & evidence

ORD record
ord-3e0dd559dc45408d914484da96d8f166
Source dataset
uspto-grants-2011_09
Patent number
US08017608B2

Reaction notes

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