2,3,5-Trimethylanisole → (4-Methoxy-2,3,6-trimethylphenyl)(5-nitro-1,3-thiazol-2-yl)methanone

HRID 435812Notes

Reaction equation

HRID 435812 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9](Cl)=[O:10])=[N:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[O:21][CH3:22].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[CH3:22][O:21][C:14]1[CH:15]=[C:16]([CH3:20])[C:17]([C:9]([C:7]2[S:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][N:6]=2)=[O:10])=[C:18]([CH3:19])[C:13]=1[CH3:12]

Participants

5

Reactant 3

HCID 885552,3,5-TrimethylanisoleHCID 6451240Aluminum(III) ChlorideHCID 148422765-Nitrothiazole-2-carbonyl chloride

Product 1

HCID 21481569(4-Methoxy-2,3,6-trimethylphenyl)(5-nitro-1,3-thiazol-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

One gram of 5-nitrothiazole-2-carboxylic acid chloride in 10 ml. of methylene chloride is combined with 850 mg. of 2,3,5-trimethylanisole and then with 1.6 g. of aluminum chloride. After three hours of agitation at room temperature, the reaction mixture is poured on 50 ml. of 1N HCl and extracted with ethyl acetate. After drying of the solution and evaporating the solvent under vacuum, the crystalline residue is recrystallized from methanol/chloroform.

Workup

  1. additionthe reaction mixture is poured on 50 ml
  2. extractionof 1N HCl and extracted with ethyl acetate
  3. customAfter drying of the solution
  4. customevaporating the solvent under vacuum
  5. customthe crystalline residue is recrystallized from methanol/chloroform

Sources & evidence

ORD record
ord-2d72e8aae1df4bf88be3a81bd9d3f0bc
Source dataset
uspto-grants-1977_02
Patent number
US04006241

Reaction notes

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