Acetic Acid → HCID 12774889, compound

HRID 848634Notes

Reaction equation

HRID 848634 reaction equation
[K].[OH:2][CH2:3][N:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[CH:6]=[N:5]1.[C:12]1([C:22](Cl)=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.C(O)(=O)C>N1C=CC=CC=1.O.C(OCC)(=O)C>[C:12]1([C:22]([O:2][CH2:3][N:4]2[C:9](=[O:10])[NH:8][C:7](=[O:11])[CH:6]=[N:5]2)=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 701461-Naphthalenecarbonyl chlorideHCID 5462222PotassiumHCID 12774884HCID 12774884, compound

Product 1

HCID 12774889HCID 12774889, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A potassium salt of 2-hydroxymethyl-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (1.81 g) is suspended in pyridine (20 ml). The mixture is ice-cooled and dropwise added with 1-naphthylcarbonyl chloride (2.48 g). After the completion of the addition, the reaction mixture is allowed to stand overnight. The pyridine is removed in vacuo from the mixture to give the residue. The residue is dissolved in water, and the resultant aqueous solution is acidified with acetic acid. The acidic aqueous solution is added with ethyl acetate (50 ml) and water (20 ml), and the ethyl acetate layer is separated and evaporated to dryness under reduced pressure. The residue is recrystallized from ethanol to give 2-(1-naphthylcarbonyloxymethyl)-3,5-dioxo-2,3,4,5-tetrahydro-1,2,4-triazine (Compound No. 43). Yield, 1.44 g (82%). M.P., 134.0° C.

Workup

  1. temperaturecooled
  2. additionAfter the completion of the addition
  3. customThe pyridine is removed in vacuo from the mixture
  4. customto give the residue
  5. customthe ethyl acetate layer is separated
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-2eeb08430b284fed8aa054761e76e625
Source dataset
uspto-grants-1981_10
Patent number
US04297129

Reaction notes

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