Hydrochloric Acid → HCID 178510523, compound

HRID 1766096Notes

Reaction equation

Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[N+:11]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([O-:13])=[O:12].[C:22]([CH2:24][C:25](OCC)=[O:26])#[N:23].C(=O)([O-])[O-].[K+].[K+].Cl>CCO>[C:22]([C:24]1[C:17]([C:16]2[CH:19]=[CH:20][CH:21]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=2)=[N:9][C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)=[N:10][C:25]=1[OH:26])#[N:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of benzamidine hydrochloride (16.4 g), 3-nitrobenzaldehyde (15.1 g), ethyl cyanoacetate (11.2 ml) and potassium carbonate (16.6 g) in abs. EtOH (250 ml) was stirred at 60° C. for 8 h. The reaction mixture was cooled to 0° C. in an ice bath. The resulting precipitate was filtered off, washed with abs. EtOH and heated in water (100° C.) until a clear solution was obtained. The solution was cooled to 50° C., acidified to pH 2 by adding 2N aq. HCl and cooled to 0° C. in an ice bath. The resulting precipitate was filtered off and washed with ice water. Residual water was removed by coevaporation with 1,4-dioxane.

Workup

filtrationThe resulting precipitate was filtered off
washwashed with abs
temperatureEtOH and heated in water (100° C.) until a clear solution
customwas obtained
temperatureThe solution was cooled to 50° C.
temperaturecooled to 0° C. in an ice bath
filtrationThe resulting precipitate was filtered off
washwashed with ice water
customResidual water was removed by coevaporation with 1,4-dioxane

Sources & evidence

ORD record: ord-a592bb73c0e7428db3dd170c888c145a
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07229990B2

Reaction notes

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