Ammonium Chloride → HCID 178450114, compound

HRID 2082750Notes

Reaction equation

HRID 2082750 reaction equation
[O:1]=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH2:15][CH:16]([CH3:18])[CH3:17])=[N:5][CH:4]=[C:3]1[C:19]#[N:20].[N-:21]=[N+:22]=[N-:23].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH2:15]([O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[NH:7][C:2](=[O:1])[C:3]([C:19]2[NH:23][N:22]=[N:21][N:20]=2)=[CH:4][N:5]=1)[CH:16]([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12793259HCID 12793259, compound

Product 1

HCID 178450114HCID 178450114, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,6-dihydro-6-oxo-2-(2-isobutoxyphenyl)-pyrimidine-5-carbonitrile (3.78 g., 0.014 mole), sodium azide (1.0 g., 0.0154 mole), and ammonium chloride (0.824 g., 0.0154 mole) in N,N-dimethylformamide was heated at 125° for 19 hours stirring. The solvent was removed under reduced pressure. The residue was treated with water (40 ml.). The mixture was acidified with 6N hydrochloric acid with stirring. The mixture was filtered and the collected solid recrystallized from glacial acetic acid to give the title compound (2.4 g., 55% yield), m.p. 230°-231°.

Workup

  1. temperaturewas heated at 125° for 19 hours
  2. customThe solvent was removed under reduced pressure
  3. additionThe residue was treated with water (40 ml.)
  4. stirringwith stirring
  5. filtrationThe mixture was filtered
  6. customthe collected solid recrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-4ffd564503124fc68863abd69fbb6657
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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