2-Aminoadamantane hydrochloride → 2-Isocyanatoadamantane

HRID 1948691Notes

Reaction equation

HRID 1948691 reaction equation
Cl.[NH2:2][CH:3]1[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2.[C:13]([O-])(O)=[O:14].[Na+].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:10]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]([CH2:5]3)[CH:3]1[N:2]=[C:13]=[O:14])[CH2:9]2

Participants

5

Reactant 3

HCID 253312-Aminoadamantane hydrochlorideHCID 94429TriphosgeneHCID 516892Sodium Bicarbonate

Product 1

HCID 128826302-IsocyanatoadamantaneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A vigorously stirred mixture of 2-aminoadamantane hydrochloride (5.01 g, 26.7 mmol), CH2Cl2 (50 mL) and satd aq NaHCO3 (50 mL) was cooled in an ice bath. After 15 min, solid triphosgene (2.64 g, 8.9 mmol) was added. The mixture was stirred in the ice bath for 30 min and the layers were separated. The aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4 and concentrated under reduced pressure to afford the title compound (3.55 g, 75%) as a white solid.

Workup

  1. temperaturewas cooled in an ice bath
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with CH2Cl2 (100 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1d23ab371e4240c0932ad24284d3ed8f
Source dataset
uspto-grants-2013_03
Patent number
US08399504B2

Reaction notes

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