1,1'-Carbonyldiimidazole → HCID 12953047, compound

HRID 904583Notes

Reaction equation

HRID 904583 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12](O)=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][CH2:16][S:17][C:3]1=2.C(N1C=CN=C1)([N:20]1C=CN=C1)=O.C(=O)(O)[O-].[Na+]>O1CCCC1.CN(C)C=O>[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]([NH2:20])=[O:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:15][CH2:16][S:17][C:3]1=2

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 516892Sodium BicarbonateHCID 12953046HCID 12953046, compound

Product 1

HCID 12953047HCID 12953047, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,10-dihydro-10-oxo-1H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid (3.0g., 0.012 mol) and 1,1'-carbonyldiimidazole (2.0 g., 0.012 mol) in tetrahydrofuran (180 ml) and dimethylformamide (3.5 ml) is refluxed under nitrogen for 5 hours. The solution is cooled in an ice-bath and anhydrous ammonia is bubbled through for 15 minutes. The mixture is stirred at ice-bath temperature for 2 hours and at room temperature for one hour. The reaction mixture is cooled and the precipitate is filtered off and washed with tetrahydrofuran. The precipitate is treated with hot 0.5 mol aqueous sodium bicarbonate solution, filtered, washed with water, washed with acetone and sucked dry to give the product (2.0 g.), mp 334° C. (dec).

Workup

  1. temperatureis refluxed under nitrogen for 5 hours
  2. temperatureThe solution is cooled in an ice-bath
  3. customanhydrous ammonia is bubbled through for 15 minutes
  4. waitat room temperature for one hour
  5. temperatureThe reaction mixture is cooled
  6. filtrationthe precipitate is filtered off
  7. washwashed with tetrahydrofuran
  8. filtrationfiltered
  9. washwashed with water
  10. washwashed with acetone
  11. customsucked dry
  12. customto give the product (2.0 g.), mp 334° C. (dec)

Sources & evidence

ORD record
ord-35375789dbed4e3aa2e30067852c9c92
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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