2'-Amino-3'-methyl-4'-methoxyacetophenone → N-(6-Acetyl-3-methoxy-2-methylphenyl)-4-(propan-2-yl)-1,3-thiazole-2-carboxamide

HRID 579611Notes

Reaction equation

HRID 579611 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11]([CH3:13])=[O:12].[CH:14]([C:17]1[N:18]=[C:19]([C:22](Cl)=[O:23])[S:20][CH:21]=1)([CH3:16])[CH3:15]>O1CCOCC1>[CH:14]([C:17]1[N:18]=[C:19]([C:22]([NH:1][C:2]2[C:7]([CH3:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=2[C:11](=[O:12])[CH3:13])=[O:23])[S:20][CH:21]=1)([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 250673162'-Amino-3'-methyl-4'-methoxyacetophenoneHCID 575787964-(Propan-2-yl)-1,3-thiazole-2-carbonyl chloride

Product 1

HCID 53482122N-(6-Acetyl-3-methoxy-2-methylphenyl)-4-(propan-2-yl)-1,3-thiazole-2-carboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of (2-amino-4-methoxy-3-methylphenyl)(methyl)ketone (18.6 g, 104 mmol) in dioxane (50 mL) was added under nitrogen to a suspension of 4-isopropylthiazole-2-carbonyl chloride in dioxane (250 mL). After 2 h at room temperature, the reaction mixture was concentrated to dryness. Then, the residue was partitioned between an aqueous solution of NaHCO3 and AcOEt, organic layer was washed with brine, dried (Na2SO4), and evaporated. The residue was triturated in diisopropyl ether, filtered off and washed with diisopropyl ether to give 30.8 g (90%) of the title product 35.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customThen, the residue was partitioned between an aqueous solution of NaHCO3 and AcOEt, organic layer
  3. washwas washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was triturated in diisopropyl ether
  7. filtrationfiltered off
  8. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-922d6972dba64ad5aecb66ca869a4f07
Source dataset
uspto-grants-2015_05
Patent number
US09040562B2

Reaction notes

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