Acetic Acid → 2-Chloro-5-phenyl-1,3-thiazole

HRID 420547Notes

Reaction equation

HRID 420547 reaction equation
N[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[ClH:13].C(O)(=O)C.N([O-])=O.[Na+]>O.O.[Cu](Cl)Cl.C(Cl)(Cl)Cl.O>[Cl:13][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8731195-Phenyl-thiazol-2-ylamineHCID 23668193Sodium Nitrite

Product 1

HCID 217888402-Chloro-5-phenyl-1,3-thiazole

Reagents, catalysts & solvents 3

HCID 61482Cupric chloride dihydrateCatalystHCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 2-amino-5-phenylthiazole described in Journal of Medicinal Chemistry, 1983, Vol. 26 (8), 1158-1163, (1.00 g; 5.67 mmol), copper (II) chloride dihydrate (1.94 g; 11.3 mmol), concentrated hydrochloric acid (8 ml) and acetic acid (8 ml) was added sodium nitrite (0.47 g; 6.80 mmol) under ice-cooling. The mixture was stirred at 40° C. for 1 hour. After returning the reaction solution to room temperature, water and chloroform were added and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (methylene chloride) to give 2-chloro-5-phenylthiazole as pale yellow crystal (0.68 g; 62%).

Workup

  1. temperaturecooling
  2. customto room temperature
  3. extractionextracted
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatograph on silica gel (methylene chloride)

Sources & evidence

ORD record
ord-cd1d8a8bf6ed4261b678782bee45a637
Source dataset
uspto-grants-2012_01
Patent number
US08097610B2

Reaction notes

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