Sodium Cyanide → HCID 86694887, compound

HRID 1401755Notes

Reaction equation

[CH2:1]([O:8][CH2:9][CH:10]1[CH2:13][C:12](=[O:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[C:18](=[O:21])([O-])[O-].[NH4+:22].[NH4+:23]>O.C(O)C>[NH:22]1[CH2:13][C:12](=[O:14])[NH:23][C:18]1=[O:21].[CH2:1]([O:8][CH2:9][CH:10]1[CH2:13][C:12](=[O:14])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-(Benzyloxymethyl)cyclobutanone 4.0 g (21 mmol), sodium cyanide 2.1 g (42 mmol) and ammonium carbonate 10.1 g (105 mmol) were added into a 100-ml eggplant-shaped flask, and the mixture was dissolved in 50 ml of 50% water/ethanol. This eggplant-shaped flask was sealed and the mixture was stirred overnight at 60° C. After opening this flask with caution in a draft chamber, the reaction solution was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and filtered to remove insoluble inorganic salts. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (hexane:ethyl acetate=50:50). Thus, 3-(benzyloxymethyl)cyclobutanone hydantoin was obtained as a white crystal (cis-form 2.8 g, 11 mmol, 50%; trans-form 1.1 g, 4.3 mmol, 21%).

Workup

customThis eggplant-shaped flask was sealed
concentrationthe reaction solution was concentrated under reduced pressure
dissolutionThe residue was dissolved in ethyl acetate
filtrationfiltered
customto remove insoluble inorganic salts
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by silica gel chromatography (hexane:ethyl acetate=50:50)

Sources & evidence

ORD record: ord-a24d7f09e4f34ef5906832174042eb2a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907128B2

Reaction notes

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