1,1'-Carbonyldiimidazole → N-methoxy-N-methyl-4-(methylthio)-benzeneacetamide

HRID 343072Notes

Reaction equation

HRID 343072 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:26][NH:27][O:28][CH3:29]>C(Cl)Cl.CCOCC>[CH3:29][O:28][N:27]([CH3:26])[C:10](=[O:12])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 49839124-(Methylthio)phenylacetic acid

Product 1

HCID 54466679N-methoxy-N-methyl-4-(methylthio)-benzeneacetamideYield 93%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(methylthio)phenylacetic acid (18.3 g, 0.100 mol) in methylene chloride (200 mL) was added 1,1'-carbonyldiimidazole (16.3 g, 0.100 mol) portionwise. The mixture was stirred at room temperature for 20 minutes, and N,O-dimethylhydroxylamine hydrochloride (9.8 g, 0.100 mol) was added. The reaction mixture was stirred overnight at room temperature, diluted with ether (500 mL) and washed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and brine. The organic layer was dried over magnesium sulfate, filtered and the filtrate was concentrated in vacuo to give 20.9 g of N-methoxy-N-methyl-4-(methylthio)-benzeneacetamide as a clear oil (93%).

Workup

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. washwashed successively with 1N hydrochloric acid, saturated aqueous sodium bicarbonate and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-62596f5f4496467392d636f32576ebdf
Source dataset
uspto-grants-1999_01
Patent number
US05859257

Reaction notes

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