Water → 3-Chloro-5-(2-methylphenyl)-1,2-thiazole-4-carboxylic acid
Reaction equation
[Cl:1][C:2]1[C:6]([C:7]#N)=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[S:4][N:3]=1.S(=O)(=O)(O)[OH:17].N([O-])=O.[Na+].[OH2:25]>>[Cl:1][C:2]1[C:6]([C:7]([OH:17])=[O:25])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])[S:4][N:3]=1Participants
5
Conditions
- Temperature
- 120 °C
Procedure
Into a 100-mL round-bottom flask, was placed 3-chloro-5-(2-methylphenyl)-1,2-thiazole-4-carbonitrile (6 g, 25.56 mmol, 1.00 equiv). This was followed by the addition of sulfuric acid (8 mL). The mixture was stirred at 120° C. for 1 h. To this was added a solution of NaNO2 (3.54 g, 51.30 mmol, 2.01 equiv) in water (5 mL) dropwise with stirring at 0° C. The resulting solution was stirred for 1 h at 50° C. in an oil bath. The resulting solution was extracted with 3×50 mL of ethyl acetate and the organic layers combined, washed with 20 mL 2N HCl, dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 5 g (crude) of 3-chloro-5-(2-methylphenyl)-1,2-thiazole-4-carboxylic acid as yellow oil.
Workup
- customInto a 100-mL round-bottom flask, was placed
- stirringwith stirring at 0° C
- stirringThe resulting solution was stirred for 1 h at 50° C. in an oil bath
- extractionThe resulting solution was extracted with 3×50 mL of ethyl acetate
- washwashed with 20 mL 2N HCl
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
- customThis resulted in 5 g (crude) of 3-chloro-5-(2-methylphenyl)-1,2-thiazole-4-carboxylic acid as yellow oil
Sources & evidence
- ORD record
- ord-981ab90418e243e49b2c81e8ccf98378
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09067898B1
Reaction notes
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