Hydrochloric Acid → HCID 178458296, compound

HRID 2082751Notes

Reaction equation

HRID 2082751 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[N-:5]=[N+:6]=[N-:7].[Na+].[O:9]=[C:10]1[NH:15][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH2:23][CH:24]=[CH2:25])=[N:13][CH:12]=[C:11]1[C:26]#[N:27].Cl>O.O1CCCC1>[CH2:23]([O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]1[NH:15][C:10](=[O:9])[C:11]([C:26]2[NH:27][N:7]=[N:6][N:5]=2)=[CH:12][N:13]=1)[CH:24]=[CH2:25]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 6451240Aluminum(III) ChlorideHCID 12793261HCID 12793261, compound

Product 1

HCID 178458296HCID 178458296, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aluminum chloride (1.71 g., 0.0128 mole) followed by sodium azide (2.5 g., 0.0384 mole) was cautiously added to ice-cold, stirred tetrahydrofuran (100 ml.). The mixture was heated under reflux for 0.5 hour. To the mixture was added 1,6-dihydro-6-oxo-2-(2-allyloxyphenyl)pyrimidine-5-carbonitrile (3.23 g., 0.0128 mole) and refluxing was continued for 18 hours. The cooled reaction mixture was diluted with water and acidified with 6N hydrochloric acid. The precipitate was collected and recrystallized from 95% ethanol to give the title compound (1.4 g., 37%), m.p. 221°-225°. Two recrystallizations from acetic acid gave analytical material, m.p. 230.5°-232° (decomp).

Workup

  1. additionwas cautiously added to ice-cold
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 0.5 hour
  4. temperaturerefluxing
  5. customThe cooled reaction mixture
  6. customThe precipitate was collected
  7. customrecrystallized from 95% ethanol

Sources & evidence

ORD record
ord-3b151f866829495290d7231149b3853e
Source dataset
uspto-grants-1978_04
Patent number
US04082751

Reaction notes

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