Ammonium Chloride → HCID 178515155, compound

HRID 1155929Notes

Reaction equation

HRID 1155929 reaction equation
[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]#[N:13])[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:14][S:15][CH2:16][C:3]1=2.[N-:17]=[N+:18]=[N-:19].[Na+].[Cl-].[NH4+]>CN(C)C=O>[O:1]=[C:2]1[N:7]2[CH:8]=[C:9]([C:12]3[NH:19][N:18]=[N:17][N:13]=3)[CH:10]=[CH:11][C:6]2=[N:5][C:4]2[CH2:14][S:15][CH2:16][C:3]1=2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12953044HCID 12953044, compound

Product 1

HCID 178515155HCID 178515155, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,10-dihydro-10-oxo-1H-pyrido[1,2-a]thieno[3,4-d]pyrimidine-7-carbonitrile (1.0 g., 0.004 mol), sodium azide (0.81 g., 0.012 mol) and ammonium chloride (0.69 g., 0.013 mol) in dimethylformamide (150 ml) is heated at 100°-105° C. for 18 hours. The solvent is removed at reduced pressure. The residue is triturated with 1 N hydrochloric acid, filtered, washed with water, dissolved in 10% aqueous potassium carbonate, filtered and reprecipitated with 1 N hydrochloric acid. The solid is filtered off and recrystallized from dimethylformamide-methanol to give a crystalline product (0.96 g.), mp 285° C.

Workup

  1. temperatureis heated at 100°-105° C. for 18 hours
  2. customThe solvent is removed at reduced pressure
  3. customThe residue is triturated with 1 N hydrochloric acid
  4. filtrationfiltered
  5. washwashed with water
  6. dissolutiondissolved in 10% aqueous potassium carbonate
  7. filtrationfiltered
  8. customreprecipitated with 1 N hydrochloric acid
  9. filtrationThe solid is filtered off
  10. customrecrystallized from dimethylformamide-methanol
  11. customto give a crystalline product (0.96 g.), mp 285° C.

Sources & evidence

ORD record
ord-b40eae4a8f4548f7a29f9b635dc8e999
Source dataset
uspto-grants-1982_06
Patent number
US04332947

Reaction notes

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