Hydrochloric Acid → HCID 178489508, compound

HRID 1971469Notes

Reaction equation

HRID 1971469 reaction equation
[C:1]([NH:3][C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH3:15])=[NH:5])#[N:2].[OH:16][CH2:17][C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O.Cl>C(#N)C.O>[CH3:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[CH2:7][NH:6][C:4]([NH:3][C:1]1[O:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:2]=1)=[NH:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 68490alpha-HydroxyacetophenoneHCID 178489513HCID 178489513, compound

Product 1

HCID 178489508HCID 178489508, compoundYield 10.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

The cyclization of 0.60 g (2.94 mmol) N-cyano-N′-(2-methoxybenzyl)guanidine with 0.44 g (2.94 mmol) 2-hydroxyacetophenone was performed in 20 ml acetonitrile and water (1:1). The pH value of the mixture was adjusted with 1 N hydrochloric acid to pH 1.5 and the mixture was then heated in the microwave at 45° C. (100 Watt) for 4.5 hours. After workup and purification, analogously to 190.2, 0.10 g of pure product was obtained.

Workup

  1. customAfter workup and purification

Sources & evidence

ORD record
ord-286f2a37edef45cbaaee9ebc771a62f1
Source dataset
uspto-grants-2013_04
Patent number
US08431604B2

Reaction notes

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