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

HRID 705435Notes

Reaction equation

HRID 705435 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:13]=[CH:12][C:10]([NH2:11])=[CH:9][CH:8]=2)[N:6]=1.[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C=O.O>[Cl:14][C:15]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:16]=1[C:17]([NH:11][C:10]1[CH:12]=[CH:13][C:7]([C:5]2[N:6]=[C:2]([CH3:1])[S:3][CH:4]=2)=[CH:8][CH:9]=1)=[O:18]

Participants

7

Reactant 4

HCID 57872,4-Dichlorobenzoic AcidHCID 81531DiisopropylethylamineHCID 1526842-Methyl-4-(4-aminophenyl)thiazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 12974802,4-dichloro-N-(4-(2-methylthiazol-4-yl)phenyl)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  1. stirringstirred for 20 minutes
  2. filtrationThe product (0.094 g, 100%) as a light yellow solid was collected via filtration

Sources & evidence

ORD record
ord-7b1a43184f874556b6106162067930e5
Source dataset
uspto-grants-2015_11
Patent number
US09174949B2

Reaction notes

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