1,1'-Carbonyldiimidazole → HCID 2813354, compound

HRID 1155915Notes

Reaction equation

HRID 1155915 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-7a3c75a0b60648b48b7197a065d21c8e
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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