Sodium Carbonate → 4-(4-Amino-2,6-dimethylphenyl)thiazol-2-amine
Reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[C:12]([CH3:13])=[CH:11][C:10]([NH:14]C(=O)C)=[CH:9][C:8]=2[CH3:18])[N:6]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl>[NH2:14][C:10]1[CH:9]=[C:8]([CH3:18])[C:7]([C:5]2[N:6]=[C:2]([NH2:1])[S:3][CH:4]=2)=[C:12]([CH3:13])[CH:11]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of N-(4-(2-aminothiazol-4-yl)-3,5-dimethylphenyl)acetamide (1.31 g, 5.0 mmol) in 2N HCl (25 mL) was refluxed for 1 h and then cooled to 0° C. Na2CO3 was carefully added to the stirring mixture until no gas evolvement, and the pH was further adjusted to 8. The mixture was then extracted with EtOAc (4×50 mL), and the combined organic phase was dried over Na2SO4, filtered, concentrated, and provided 4-(4-amino-2,6-dimethylphenyl)thiazol-2-amine (1.03 g, 93.9% yield). The crude product was used for next reaction without further purification.
Workup
- extractionThe mixture was then extracted with EtOAc (4×50 mL)
- dry with materialthe combined organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-fb2f301b41e44ffea570d806e3ad1607
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09422275B2
Reaction notes
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