Sodium Carbonate → (R)-tetrahydrofuran-2-ylmethyl-cyanamide

HRID 536715Notes

Reaction equation

HRID 536715 reaction equation
[N:1]#[C:2]Br.[C:4]([O-:7])([O-])=O.[Na+].[Na+].O1[CH2:14][CH2:13][CH2:12][C@@H:11]1[NH:15]C>CCOCC>[O:7]1[CH2:4][CH2:14][CH2:13][C@@H:12]1[CH2:11][NH:15][C:2]#[N:1]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 66643034(R)-(tetrahydro-furan-2-yl)-methylamine

Product 1

HCID 55288151(R)-tetrahydrofuran-2-ylmethyl-cyanamideYield 88.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of cyanogen bromide (2.2 g, 20.8 mmol) and anhydrous Na2CO3 (4.2 g, 39.6 mmol) in dry ether (30 mL) cooled between −20 and −10° C. was added (R)-(tetrahydro-furan-2-yl)-methylamine (Aldrich) (2.0 g, 19.8 mmol) over 10 minutes. Stirring was continued for an additional 1.5 hours at −20 to −10° C. Then the mixture was filtered and concentrated to provide 2.21 g of the title product. MS (ESI) m/z 127 (M+H)+.

Workup

  1. temperaturecooled between −20 and −10° C.
  2. filtrationThen the mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-121bee5cdc904dc5a152afc592128e76
Source dataset
uspto-grants-2014_10
Patent number
US08859596B2

Reaction notes

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