Methanol → N-[(2,4-dichlorophenyl)methyl]-1,3,3-trimethyl-5-oxoprolinamide

HRID 554143Notes

Reaction equation

HRID 554143 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N+:10]#[C-:11].[CH3:12][C:13]([CH3:20])([CH:18]=O)[CH2:14][C:15](O)=[O:16].[CH3:21][NH2:22].C[OH:24]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][NH:10][C:11](=[O:24])[C@@H:18]1[C:13]([CH3:20])([CH3:12])[CH2:14][C:15](=[O:16])[N:22]1[CH3:21]

Participants

5

Reactant 4

HCID 887MethanolHCID 6329MethylamineHCID 27580712,4-Dichloro-1-(isocyanomethyl)benzeneHCID 247680973-Formyl-3-methylbutanoic acid

Product 1

HCID 67460084N-[(2,4-dichlorophenyl)methyl]-1,3,3-trimethyl-5-oxoprolinamide

Conditions

Temperature
100 °C

Procedure

To a solution of (2,4-dichlorophenyl)methyl isocyanide (0.094 g, 0.5 mmol) and 3,3-dimethyl-4-oxobutanoic acid (0.065 mg, 0.5 mmol, prepared as described below) in methanol (2 ml) was added methylamine (0.080 ml, 33% solution in ethanol). The mixture was heated to 100° C. for 30 minutes in a microwave reactor. The solvent was removed in vacuo and the residue was purified by mass-directed automated HPLC to give a colourless gum which was triturated with diethyl ether to give N-[(2,4-dichlorophenyl)methyl]-1,3,3-trimethyl-5-oxoprolinamide (0.043 g) as a sticky white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified
  3. customto give a colourless gum which
  4. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-d4b70d2f4dee4c34a21b077ae3a72e42
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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