p-Anisoyl chloride → N-(4,5-Diphenyl-thiazol-2-yl)-4-methoxy-benzamide

HRID 533983

Reaction equation

HRID 533983 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH2:18])[S:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1.C(N(CC)CC)C>O1CCOCC1>[C:1]1([C:7]2[N:8]=[C:9]([NH:18][C:25](=[O:26])[C:24]3[CH:28]=[CH:29][C:21]([O:20][CH3:19])=[CH:22][CH:23]=3)[S:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 732222-Amino-4,5-diphenylthiazole

Product 1

HCID 3112498N-(4,5-Diphenyl-thiazol-2-yl)-4-methoxy-benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4,5-Diphenyl-thiazol-2-ylamine (50.5 mg, 0.200 mmol) and 4-methoxy-benzoyl chloride (34.1 mg, 0.200 mmol) were dissolved in 1,4-dioxane (2 mL) containing triethylamine (84.1 μL, 0.600 mmol). The reaction mixture was stirred overnight at room temperature. The crude product was filtered, evaporated to dryness, dissolved in 1 mL of dimethylsulfoxide and purified by reverse-phase preparative liquid chromatography (12.5 mg, 0.0323 mmol, 16.2%). ESI-MS m/z calc. 386.1. found 387.2 (M+1)+ Retention time 3.95 minutes.

Workup

  1. filtrationThe crude product was filtered
  2. customevaporated to dryness
  3. dissolutiondissolved in 1 mL of dimethylsulfoxide
  4. custompurified by reverse-phase preparative liquid chromatography (12.5 mg, 0.0323 mmol, 16.2%)

Sources & evidence

ORD record
ord-44c566a4a2bd4a8b9d8466a6a9483ef4
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Linked notes

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