Hydrochloric Acid → HCID 13588447, compound

HRID 1285226Notes

Reaction equation

HRID 1285226 reaction equation
[C:1]([CH:3]1[NH:7][CH:6]=[N:5][C:4]1=[N:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:2].C([O-])(=O)C.[Na+].C(O)(=O)C.C([BH3-])#N.[Na+].[OH-].[Na+].Cl>CO.C(O)(=O)C>[C:1]([C:3]1[NH:7][CH:6]=[N:5][C:4]=1[NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)#[N:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 23662384Sodium DiacetateHCID 178510596HCID 178510596, compound

Product 1

HCID 13588447HCID 13588447, compoundYield 30.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a stirred solution of 5-cyano-4-phenylmethylimino-1H-imidazole (0.7 g, 0.004 mole) in 10 ml of methanol was added 5 ml of a 1M sodium acetate/acetic acid buffer (pH=6), followed by sodium cyanoborohydride (0.5 g, 0.008 mole). The pH of the reaction mixture was adjusted to 6 by the dropwise addition of acetic acid. The reaction mixture was stirred at ambient temperature for 17 hours, and the pH was adjusted to 10 with aqueous 5% sodium hydroxide. The pH of the reaction mixture was readjusted to 6 with aqueous 2N hydrochloric acid and the mixture extracted with four 50 ml portions of diethyl ether. The combined yellow extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residual oil. The oil was chromatographed on a column using silica gel as the stationary phase and diethyl ether as the eluant, to give 5-cyano-4-phenylmethylamino-1H-imidazole (0.24 g; mp, 95°-97° ).

Workup

  1. extractionthe mixture extracted with four 50 ml portions of diethyl ether
  2. dry with materialThe combined yellow extracts were dried with magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure to a residual oil
  5. customThe oil was chromatographed on a column

Sources & evidence

ORD record
ord-e44fc03bb4c047af849f250f760d7277
Source dataset
uspto-grants-1986_01
Patent number
US04565875

Reaction notes

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