Triethylamine → 4-Methyl-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzamide

HRID 533984Notes

Reaction equation

HRID 533984 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]([NH2:12])[S:10][CH:11]=2)=[CH:3][CH:2]=1.[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=1.C(N(CC)CC)C>O1CCOCC1>[CH3:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:12][C:9]2[S:10][CH:11]=[C:7]([C:4]3[CH:3]=[CH:2][C:1]([CH3:13])=[CH:6][CH:5]=3)[N:8]=2)=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 134054-Methylbenzoyl ChlorideHCID 2440664-(4-Methylphenyl)-1,3-thiazol-2(3H)-imine

Product 1

HCID 5773564-Methyl-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-p-Tolyl-thiazol-2-ylamine (38.1 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 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 (13.5 mg, 0.0438, 21.9%). ESI-MS m/z calc. 308.1. found 309.0 (M+1)+ Retention time 3.72 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 (13.5 mg, 0.0438, 21.9%)

Sources & evidence

ORD record
ord-b707d695d90d4eca86e0d0ac4e4f33dd
Source dataset
uspto-grants-2014_10
Patent number
US08853415B2

Reaction notes

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