(4-Chlorophenyl)ethanimidamide--hydrogen chloride (1/1) → HCID 178479719, compound

HRID 1027479Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH2:12])=[NH:11])=[CH:5][CH:4]=1.C([O:15][C:16](=O)[CH:17]([NH:23][C:24](=[O:32])[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=1)[C:18](OCC)=[O:19])C>C(O)C>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]2[N:12]=[C:16]([OH:15])[C:17]([NH:23][C:24](=[O:32])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=3)=[C:18]([OH:19])[N:11]=2)=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

2.25 g of sodium were dissolved in 140 ml of ethanol at 60° C. to give a solution of sodium ethoxide. 6.9 g of 2-(4-chloro-phenyl)acetamidine hydrochloride were added while the temperature was maintained at 60° C. The mixture was stirred for 10 min, and then a solution of 10 g of 2-(3-fluoro-benzoylamino)-malonic acid diethyl ester in 20 ml of ethanol was added. The reaction mixture was stirred at 60° C. for 3 h and then evaporated to dryness. The residue was dissolved in the minimum amount of water, and the pH was adjusted to 1-2 by addition of concentrated aqueous hydrochloric acid. The precipitate was filtered off and dried in an infrared dryer until constant weight. 8.9 g of the title compound were obtained.

Workup

stirringThe reaction mixture was stirred at 60° C. for 3 h
customevaporated to dryness
dissolutionThe residue was dissolved in the minimum amount of water
additionthe pH was adjusted to 1-2 by addition of concentrated aqueous hydrochloric acid
filtrationThe precipitate was filtered off
customdried in an infrared dryer until constant weight

Sources & evidence

ORD record: ord-2634c4daaeeb49679361418cb9655a50
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735387B2

Reaction notes

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