Hydrochloric Acid → HCID 178437000, compound

HRID 1704828Notes

Reaction equation

HRID 1704828 reaction equation
[CH2:1]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2=[N:13][CH:14]=[C:15]([C:18]#[N:19])[C:16](=[O:17])[N:5]2[CH2:4]1)[CH3:2].[N-:20]=[N+:21]=[N-:22].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O.O>[CH2:1]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2=[N:13][CH:14]=[C:15]([C:18]3[NH:22][N:21]=[N:20][N:19]=3)[C:16](=[O:17])[N:5]2[CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 22758817HCID 22758817, compound

Product 1

HCID 178437000HCID 178437000, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (±)-7-ethyl-6,7-dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carbonitrile (208 mg., 0.836 mmole), sodium azide (59.8 mg., 0.92 mmole), and ammonium chloride (49.1 mg., 0.92 mmole) in N,N-dimethylformamide (2 ml.) was stirred for 19 hours at an oil bath temperature of 120°. The mixture was diluted with water and acidified with dilute hydrochloric acid to precipitate 215 mg. (87% yield) of the tetrazole, m.p. 254°-258° with decomposition. Recrystallization from acetic acid provided pale yellow crystals of the analytical sample, m.p. 282°-283.5° with decomposition.

Workup

  1. customto precipitate 215 mg

Sources & evidence

ORD record
ord-2e75074b3c0c49eba28ea8da6cf3ec0e
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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