Ethanol → HCID 12953041, compound

HRID 1577432Notes

Reaction equation

HRID 1577432 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][S:16][CH2:17][C:3]1=2.C(N1C=CN=C1)(N1[CH:24]=[CH:23]N=C1)=O.C(O)C.C(=O)(O)[O-].[Na+]>CN(C)C=O.O1CCCC1>[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([O:14][CH2:23][CH3:24])=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][S:16][CH2:17][C:3]1=2

Participants

7

Reactant 4

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 12953042HCID 12953042, compound

Product 1

HCID 12953041HCID 12953041, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,10-dihydro-10-oxo-1H-pyrido[1,2-a]thieno-[3,4-d]pyrimidine-7-carboxylic Acid (15 g., 0.06 mol) and 1,1' carbonyldiimidazole (9.8 g, 0.06 mol) in dimethylformamide (12 ml) and tetrahydrofuran (700 ml) is refluxed with stirring for 3 hours. Absolute ethanol (20 ml) is added and refluxing is continued for a further 3 hours. The solvents are removed under reduced pressure. The residue is shaken with hot 0.5 mol aqueous sodium bicarbonate (200 ml), cooled and filtered. The residue is washed several times with water and recrystallized from methanol to give the product (8.9 g.) mp 183°-185° C.

Workup

  1. temperatureis refluxed
  2. temperaturerefluxing
  3. waitis continued for a further 3 hours
  4. customThe solvents are removed under reduced pressure
  5. temperaturecooled
  6. filtrationfiltered
  7. washThe residue is washed several times with water
  8. customrecrystallized from methanol
  9. customto give the product (8.9 g.) mp 183°-185° C.

Sources & evidence

ORD record
ord-6a69d6e25e9b4b2caab83cfe56d3bde7
Source dataset
uspto-grants-1981_09
Patent number
US04287340

Reaction notes

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