Hydrochloric Acid → HCID 178458271, compound

HRID 1863134Notes

Reaction equation

HRID 1863134 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:19][CH2:20][CH2:21][CH3:22])=[C:7]([C:9]2[N:17]=[C:16]3[C:12](=[N:13][N:14]=[N:15]3)[C:11](=[O:18])[N:10]=2)[CH:8]=1)#[N:2].[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].Cl>O.CN1CCCC1=O>[CH2:20]([O:19][C:6]1[CH:5]=[CH:4][C:3]([C:1]2[NH:25][N:24]=[N:23][N:2]=2)=[CH:8][C:7]=1[C:9]1[N:17]=[C:16]2[C:12](=[N:13][N:14]=[N:15]2)[C:11](=[O:18])[N:10]=1)[CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20392959HCID 20392959, compound

Product 1

HCID 178458271HCID 178458271, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 2-(5-cyano-2-propoxyphenyl)-8-azapurin-6-one (2.0 g), sodium azide (1.05 g), ammonium chloride (0.9 g) and N-methylpyrrolid-2-one (16 ml) was cautiously heated, with stirring, in a sealed flask for 7 hours at 100°-110° C. The mixture was then cooled and added to water (80 ml) and the mixture was acidified by treatment with concentrated hydrochloric acid. The solid which separated was filtered off and recrystallised from acetic acid to give 2-[2-propoxy-5-(tetrazol-5-yl)phenyl]-8-azapurin-6-one (0.65 g), m.p. 253°-259° C. (with decomposition).

Workup

  1. temperaturewas cautiously heated
  2. temperatureThe mixture was then cooled
  3. customThe solid which separated
  4. filtrationwas filtered off
  5. customrecrystallised from acetic acid

Sources & evidence

ORD record
ord-11347122a2064313a7993610cc1356b9
Source dataset
uspto-grants-1979_09
Patent number
US04167568

Reaction notes

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