Nitric Acid → HCID 13546655, compound

HRID 450103Notes

Reaction equation

HRID 450103 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:12]([O-])([OH:14])=[O:13]>S(=O)(=O)(O)O>[N+:12]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2[S:8][CH:9]=[CH:10][N:11]=2)=[CH:6][CH:5]=1)([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5474942-Phenylthiazole

Product 1

HCID 13546655HCID 13546655, compoundYield 58.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-phenyl thiazole (200 mg, 1.24 mmol) in conc. sulphuric acid (0.5 ml) was cooled to 0° C. The nitrating mixture (made up of 0.5 ml of conc. nitric acid and 0.5 ml of conc. sulfuric acid) was added dropwise and stirred at 0° C. for 1 hr. The reaction was quenched with ice water and basified with sodium hydroxide solution. The resultant precipitate was filtered and washed with water. Purification by column chromatography over silica gel using EtOAc/pet ether gave 2-(4-nitrophenyl) thiazole (150 mg, 58.6%) as solid.

Workup

  1. customThe reaction was quenched with ice water
  2. filtrationThe resultant precipitate was filtered
  3. washwashed with water
  4. customPurification by column chromatography over silica gel

Sources & evidence

ORD record
ord-82233c35ac9a4cfabafb1905450f01d6
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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