Triethylamine → HCID 19862606, compound

HRID 1165171Notes

Reaction equation

HRID 1165171 reaction equation
C(N(CC)CC)C.Cl.[CH2:9]([C:11]1[N:12]([CH3:19])[CH:13]=[CH:14][C:15](=[O:18])[C:16]=1[OH:17])[CH3:10].[N:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:21]=[O:22]>C(#N)C.C(Cl)Cl>[CH2:27]([O:26][C:24]([CH2:23][NH:20][C:21]([O:17][C:16]1[C:15](=[O:18])[CH:14]=[CH:13][N:12]([CH3:19])[C:11]=1[CH2:9][CH3:10])=[O:22])=[O:25])[CH3:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetateHCID 198626002-Ethyl-3-hydroxy-1-methylpyridin-4(1H)-one--hydrogen chloride (1/1)

Product 1

HCID 19862606HCID 19862606, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

2.8 ml of triethylamine are added at room temperature to a suspension of 1.89 g of 2-ethyl-3-hydroxy-1-methyl-4(1H)-pyridinone hydrochloride in 50 ml of acetonitrile and 50 ml of methylene chloride followed by the addition of 2.27 ml of ethyl isocyanatoacetate. The ensuing reaction is slightly exothermic and a solution forms within 10 minutes. The reaction is complete after 1.5 hours. The reaction mixture is evaporated to dryness under reduced pressure, the residue is dried under a high vacuum and crystallised from ethyl acetate. A solution of 4.0 g of the resultant hydrochloride of 3-(ethoxycarbonylmethylaminocarbonyloxy)-2-ethyl-1-methyl-4(1H)-pyridinone in 40 ml of water is adjusted to pH 2.5 with phosphoric acid, saturated with sodium chloride and extracted with methylene chloride. The residue of the organic extract is crystallised from a 95:5 mixture of ethyl acetate and methylene chloride, affording 3-(ethoxycarbonylmethylaminocarbonyloxy)-2-ethyl-1-methyl-4(1H)-pyridinone with a melting point of 99°-100° C.

Workup

  1. customThe ensuing reaction
  2. waitThe reaction is complete after 1.5 hours
  3. customThe reaction mixture is evaporated to dryness under reduced pressure
  4. customthe residue is dried under a high vacuum
  5. customcrystallised from ethyl acetate
  6. extractionextracted with methylene chloride
  7. extractionThe residue of the organic extract
  8. customis crystallised from a 95:5 mixture of ethyl acetate and methylene chloride

Sources & evidence

ORD record
ord-886c8d82dce247809bd15b168856d92e
Source dataset
uspto-grants-1990_03
Patent number
US04908371

Reaction notes

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