2,4-Dichlorobenzoic Acid → 2,4-dichloro-N-(4-(2-methylthiazol-4-yl)phenyl)benzamide

Participants

Role	Name	HCID	Charge
Reactant	2,4-Dichlorobenzoic Acid	HCID 5787	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Methyl-4-(4-aminophenyl)thiazole	HCID 152684	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2,4-dichloro-N-(4-(2-methylthiazol-4-yl)phenyl)benzamide	HCID 1297480	—

Reaction Steps

To a solution of 4-(2-methylthiazol-4-yl)aniline (0.05 g, 0.26 mmol) and 2,4-dichlorobenzoic acid (0.05 g, 0.26 mmol) in dimethylformamide (20 mL) and diisopropylethylamine (0.067 g, 0.09 mL, 0.52 mmol) at room temperature was added HATU (0.148 g, 0.39 mmol) in one portion. The reaction was stirred at room temperature for 4 hours, then poured in to water (200 mL) and stirred for 20 minutes. The product (0.094 g, 100%) as a light yellow solid was collected via filtration. LC-MS (M+H): 364. 1H NMR (400 MHz, dmso-d6): 10.67 (s, 1H), 7.95 (d, 2H), 7.87 (s, 1H), 7.80-7.77 (m, 3H), 7.69-7.58 (m, 2H), 2.74 (s, 3H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09174949B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-7b1a43184f874556b6106162067930e5
Source note	uspto-grants-2015_11