Ammonium Chloride → HCID 178466175, compound

HRID 2082748Notes

Reaction equation

HRID 2082748 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][CH3:16])=[N:5][CH:4]=[C:3]1[C:17]#[N:18].[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+]>>[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:17]2[NH:21][N:20]=[N:19][N:18]=2)=[CH:4][N:5]=1)[CH3:16]

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12793255HCID 12793255, compound

Product 1

HCID 178466175HCID 178466175, compoundYield 50%

Procedure

A mixture of 1,6-dihydro-6-oxo-2-(2-ethoxyphenyl) pyrimidine-5-carbonitrile (2.17 g., 9.0 mmole), sodium azide (0.645 g., 9.9 mmole), and ammonium chloride (0.53 g., 9.9 mmole) in dry, N,N-dimethylformamide (18 ml.) was stirred at 125° for 16 hours. The solvent was removed under reduced pressure. The residue was treated with water and the resulting slurry acidified with 1N hydrochloric acid. The mixture was filtered. The collected solid was washed with water, dried, and recrystallized from glacial acetic acid to give the title compound (1.28 g., 50% yield). An analytical sample had m.p. 289°-290° with decomposition.

Workup

  1. customin dry
  2. customThe solvent was removed under reduced pressure
  3. additionThe residue was treated with water
  4. filtrationThe mixture was filtered
  5. washThe collected solid was washed with water
  6. customdried
  7. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-23424de8aa4745dc9b428ac97668b712
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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