Sulfuric Acid → HCID 90418268, compound

HRID 2177295Notes

Reaction equation

HRID 2177295 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][N:12]=[C:11](C)[C:10]=1C#N.S(=O)(=O)(O)O.N([O-])=O.[Na+].[CH3:26][C:27](=[O:31])[O:28]CC>>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[S:13][N:12]=[C:11]([CH3:10])[C:26]=1[C:27]([OH:28])=[O:31]

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 23668193Sodium NitriteHCID 90418458HCID 90418458, compound

Product 1

HCID 90418268HCID 90418268, compound

Conditions

Temperature
120 °C

Procedure

Into a 25-mL round-bottom flask, was placed 5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazole-4-carbonitrile (200 mg, 0.86 mmol, 1.00 equiv). This was followed by the addition of sulfuric acid (conc.) (10 mL). The mixture was stirred for 1 h at 120° C. To this was added NaNO2 (aq) (201 mg) at 0-5° C. The resulting solution was stirred for 30 min at 50° C. The resulting solution was diluted with 50 mL of EA. The organic phase was washed with 1×20 mL of 2N HCl and 1×20 mL brine. The mixture was dried over anhydrous sodium sulfate and concentrated. This resulted in 180 mg (crude) of 5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazole-4-carboxylic acid as a yellow oil.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred for 30 min at 50° C
  3. washThe organic phase was washed with 1×20 mL of 2N HCl and 1×20 mL brine
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThis resulted in 180 mg (crude) of 5-(2-fluoro-4-methylphenyl)-3-methyl-1,2-thiazole-4-carboxylic acid as a yellow oil

Sources & evidence

ORD record
ord-7f06f589b09f4e3fbdda2ebaedc05d2a
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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