Water → HCID 90418039, compound

HRID 2177299Notes

Reaction equation

[CH2:1]([C:3]1[C:7]([C:8]#N)=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=2[F:17])[S:5][N:4]=1)[CH3:2].N([O-])=[O:19].[Na+].[OH2:22]>CC(=O)OCC>[CH2:1]([C:3]1[C:7]([C:8]([OH:19])=[O:22])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=2[F:17])[S:5][N:4]=1)[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 25-mL round-bottom flask, was placed 3-ethyl-5-(2-fluoro-4-methylphenyl)-1,2-thiazole-4-carbonitrile (200 mg, 0.81 mmol, 1.00 equiv). This was followed by the addition of sulfuric acid(conc.) (10 mL). The mixtures were stirred for 1 h at 120° C. To this was added a solution of NaNO2(aq) (168 mg, 2.43 mmol, 3 equiv) in water (0.5 mL) 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. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 150 mg (crude) of 3-ethyl-5-(2-fluoro-4-methylphenyl)-1,2-thiazole-4-carboxylic acid as a yellow solid.

Workup

customInto a 25-mL round-bottom flask, was placed
stirringThe resulting solution was stirred for 30 min at 50° C
washThe organic phase was washed with 1×20 mL of 2N HCl and 1×20 mL brine
dry with materialThe mixture was dried over anhydrous sodium sulfate
filtrationThe solids were filtered out
concentrationThe resulting mixture was concentrated under vacuum
customThis resulted in 150 mg (crude) of 3-ethyl-5-(2-fluoro-4-methylphenyl)-1,2-thiazole-4-carboxylic acid as a yellow solid

Sources & evidence

ORD record: ord-141dc8ab2328414c83cd4fa972ea2edf
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067898B1

Reaction notes

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