1,1'-Carbonyldiimidazole → HCID 2813354, compound

HRID 904567Notes

Reaction equation

HRID 904567 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[CH:15]=[CH:16][S:17][C:3]1=2.C(N1C=CN=C1)([N:20]1C=CN=C1)=O>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[CH:15]=[CH:16][S:17][C:3]1=2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 2813353HCID 2813353, compound

Product 1

HCID 2813354HCID 2813354, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10-oxo-10H-pyrido[1,2-a]thieno[3,2-d]pyrimidine-7-carboxylic acid (2.5 g, 0.01 mol) and 1,1'-carbonyldiimidazole (1.7 g, 0.01 mol) in dimethylformamide (25 ml) is heated at 90°-95° C. for one hour under nitrogen. 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. The precipitate is washed with tetrahydrofuran and recrystallized from dimethylformamide to give the product (1.2 g.), mp 319°-320° C.

Workup

  1. temperatureis heated at 90°-95° C. for one hour under nitrogen
  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. washThe precipitate is washed with tetrahydrofuran
  8. customrecrystallized from dimethylformamide
  9. customto give the product (1.2 g.), mp 319°-320° C.

Sources & evidence

ORD record
ord-fcd4cb873f844f2d9db6d221761574d8
Source dataset
uspto-grants-1980_10
Patent number
US04230707

Reaction notes

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