Nitric Acid → Ethyl 2-iodo-4-(trifluoromethyl)-5-thiazolecarboxylate

HRID 2049937Notes

Reaction equation

HRID 2049937 reaction equation
N[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.P(=O)(O)(O)O.[N+]([O-])(O)=O.N([O-])=O.[Na+].[I-:29].[K+]>O>[I:29][C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1

Participants

7

Reactant 5

HCID 944Nitric AcidHCID 1004Phosphoric AcidHCID 4875Potassium IodideHCID 676565-Thiazolecarboxylic acid, 2-amino-4-(trifluoromethyl)-, ethyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 13593392Ethyl 2-iodo-4-(trifluoromethyl)-5-thiazolecarboxylateYield 25.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a cold (-5° C.) solution of 4.0 g (0.0166 mole) of ethyl 2-amino-4-trifluoromethyl-5-thiazolecarboxylate, prepared according to U.S. Pat. No. 2,726,237, in 30 ml. of 85% phosphoric acid and 30 ml. of 70% nitric acid was added a solution of 1.26 g (0.0166 mole) of sodium nitrite in 10 ml. of water in 10 minutes. The reaction mixture was stirred for 10 minutes and poured into a solution of 10 g of potassium iodide in 100 ml. of water. The reaction mixture was stirred overnight and extracted with ether. The ether solution was dried and concentrated and the residue was chromatographed on silica gel to give 1.5 g of the desired product, m.p. 75°-76° C.

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. extractionextracted with ether
  3. dry with materialThe ether solution was dried
  4. concentrationconcentrated
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-2e1837b23a614d319ea7fa084167fe0c
Source dataset
uspto-grants-1980_04
Patent number
US04199506

Reaction notes

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