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

HRID 554100Notes

Reaction equation

HRID 554100 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])([CH2:17][CH:18]=O)[C:14](O)=[O:15].[CH2:21]([NH2:23])[CH3:22].C[OH:25]>>[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:25])[C@@H:18]1[CH2:17][C:13]([CH3:20])([CH3:12])[C:14](=[O:15])[N:23]1[CH2:21][CH3:22]

Participants

5

Reactant 4

HCID 887MethanolHCID 6341EthylamineHCID 27580712,4-Dichloro-1-(isocyanomethyl)benzeneHCID 212457072,2-Dimethyl-4-oxobutanoic acid

Product 1

HCID 67462193N-[(2,4-dichlorophenyl)methyl]-1-ethyl-4,4-dimethyl-5-oxoprolinamide

Conditions

Temperature
100 °C

Procedure

(2,4-Dichlorophenyl)methyl isocyanide (0.075 g, 0.4 mmol) and crude 2,2-dimethyl-4-oxobutanoic acid (0.115 g, 0.6 mmol) were dissolved in methanol (2 ml). Ethylamine solution (2M in water, 0.3 ml, 0.6 mmol) was added and the mixture was heated in a sealed vessel at 100° C. for 30 minutes in a microwave reactor. The mixture was left to stand over the weekend and then the solvent was removed in vacuo and the resulting orange oil was purified by mass-directed automated HPLC to give a clear oily gum which was triturated with diethyl ether to give N-[(2,4-dichlorophenyl)methyl]-1-ethyl-4,4-dimethyl-5-oxoprolinamide as a white solid (0.024 g). LC/MS [M+H]+=343, retention time=2.57 minutes.

Workup

  1. waitThe mixture was left
  2. customthe solvent was removed in vacuo
  3. customthe resulting orange oil was purified
  4. customto give a clear oily gum which
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-d194ff1df73d45daaa094c462283fcb1
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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