Triethylamine → N-(4,5-Diphenyl-thiazol-2-yl)-4-methyl-benzamide

HRID 533982

Reaction equation

HRID 533982 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][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1.C(N(CC)CC)C>O1CCOCC1>[C:1]1([C:7]2[N:8]=[C:9]([NH:18][C:24](=[O:25])[C:23]3[CH:27]=[CH:28][C:20]([CH3:19])=[CH:21][CH:22]=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 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 732222-Amino-4,5-diphenylthiazole

Product 1

HCID 3112499N-(4,5-Diphenyl-thiazol-2-yl)-4-methyl-benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4,5-Diphenyl-thiazol-2-ylamine (50.5 mg, 0.200 mmol) and 4-methyl-benzoyl chloride (30.9 mg, 0.200 mmol) were dissolved in 1,4-dioxane (2 mL) containing triethylamine (84.1 μL, 0.600 mmol). The reaction mixture was subjected to microwave irradiation for 5 minutes at 200° C. The crude product was filtered, evaporated to dryness, dissolved in 1 mL of dimethylsulfoxide and purified by reverse-phase preparative liquid chromatography (18.6 mg, 0.0502 mmol, 25.1%). ESI-MS m/z calc. 370.1. found 371.2 (M+1)+ Retention time 4.13 minutes.

Workup

  1. customirradiation for 5 minutes at 200° C
  2. filtrationThe crude product was filtered
  3. customevaporated to dryness
  4. dissolutiondissolved in 1 mL of dimethylsulfoxide
  5. custompurified by reverse-phase preparative liquid chromatography (18.6 mg, 0.0502 mmol, 25.1%)

Sources & evidence

ORD record
ord-a51524f04b92443e8e667dbfd87938b4
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Linked notes

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