Triethylamine → HCID 19862602, compound

HRID 1165172Notes

Reaction equation

HRID 1165172 reaction equation
C(N(CC)CC)C.[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][O:18][CH3:19])[C:10]=1[CH3:20].[N:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:22]=[O:23]>C(#N)C.C(Cl)Cl>[CH2:28]([O:27][C:25]([CH2:24][NH:21][C:22]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]([CH2:16][CH2:17][O:18][CH3:19])[C:10]=1[CH3:20])=[O:23])=[O:26])[CH3:29]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetateHCID 863453-Hydroxy-1-(2-methoxyethyl)-2-methyl-4-pyridinone

Product 1

HCID 19862602HCID 19862602, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

5.60 ml of triethylamine are added to a mixture of 5.49 g of 3-hydroxy-1-(2-methoxyethyl)-2-methyl-4(1H)-pyridinone in 150 ml of acetonitrile and 150 ml of methylene chloride, followed by the addition of 6.83 ml of ethyl isocyanatoacetate at room temperature. The slightly exothermic reaction, in the course of which a solution forms within 10 minutes, is complete after 3 hours. The solvent is removed under reduced pressure and the residue is dried under a high vacuum and crystallised from ethyl acetate. The mother liquor is discarded. 1 g of the pale beige product is partitioned between methylene chloride and water. The bulk of the product is present in the aqueous phase, which is concentrated by evaporation. The residue is dissolved in methanol and the solution is treated with activated carbon and concentrated by evaporation. The residue is crystallised from ethyl acetate, to give white crystalline 3-(ethoxycarbonylmethylaminocarbonyloxy)-1-(2-methoxyethyl)-2-methyl-4(1H)-pyridinone with a melting point of 134°-135° C.

Workup

  1. customThe slightly exothermic reaction
  2. waitis complete after 3 hours
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is dried under a high vacuum
  5. customcrystallised from ethyl acetate
  6. custom1 g of the pale beige product is partitioned between methylene chloride and water
  7. concentrationis concentrated by evaporation
  8. dissolutionThe residue is dissolved in methanol
  9. additionthe solution is treated with activated carbon
  10. concentrationconcentrated by evaporation
  11. customThe residue is crystallised from ethyl acetate

Sources & evidence

ORD record
ord-bb4899877b83408b9f705457a99e516d
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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