Cyanamide → 1-Adamantanecarbonyl Cyanamide

HRID 1824014Notes

Reaction equation

HRID 1824014 reaction equation
[N:1]#[C:2][NH2:3].[C:4]12([C:14](Cl)=[O:15])[CH2:13][CH:8]3[CH2:9][CH:10]([CH2:12][CH:6]([CH2:7]3)[CH2:5]1)[CH2:11]2>[OH-].[Na+].CCOCC>[C:4]12([C:14]([NH:1][C:2]#[N:3])=[O:15])[CH2:11][CH:10]3[CH2:9][CH:8]([CH2:7][CH:6]([CH2:12]3)[CH2:5]1)[CH2:13]2

Participants

5

Reactant 2

HCID 9864CyanamideHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 140546301-Adamantanecarbonyl CyanamideYield 78.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of cyanamide (2.52 g, 0.06 mol) in 24 ml of sodium hydroxide (10%) was added slowly to a solution of 1-adamantanecarbonylchloride (4 g, 0.02 mol) in ether (15 ml). The reaction mixture was stirred at room temperature overnight. The reaction mixture was extracted with ether and the aqueous layer was cooled in ice bath and acidified with hydrochloric acid (10%) to pH 2. The precipitated white solid was filtered, washed with water, later hexanes and dried under high vacuum to give the N-(1-adamantancarbonyl)cyanamide (3.2 g, 78%); m.p. 164–166° C. (lit m.p. 168–170° C.); purity 94% HPLC; 1H-NMR (CD3OD) δ 1.45–2.16 (m, 15H, CH2 and CH).

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. temperaturethe aqueous layer was cooled in ice bath
  3. filtrationThe precipitated white solid was filtered
  4. washwashed with water, later hexanes
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d3e942eb04c74e7cb402a440422c0502
Source dataset
uspto-grants-2006_05
Patent number
US07041702B1

Reaction notes

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