Triphosgene → 884504-55-6

HRID 2171289Notes

Reaction equation

HRID 2171289 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])([CH3:5])([CH3:4])[CH3:3].Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.C([O-])(O)=O.[Na+].O>[N:10]([CH2:9][CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:11])=[C:13]=[O:15]

Participants

6

Reactant 2

HCID 94429TriphosgeneHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

Product 1

HCID 44721307884504-55-6Yield 93.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

β-Alanine tert-butyl ester hydrochloride (13.0, 71.6 mmol) in CH2Cl2 (240 mL) and saturated NaHCO3(aq) solution (240 mL) was degassed and the flask was cooled in ice water bath. Triphosgene (21.2 g, 71.6 mmol) was added in one portion under inert atmosphere at 0° C. The reaction stirred at 0° C. to RT over 2.5 hr. The reaction was diluted with water (500 mL) and poured into reparatory funnel. The layers separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to obtain crude tert-butyl 3-iso cyanatopropionate (11.5 g) as a yellow liquid. This crude material was directly used for next reaction without purification. 1H NMR (300 MHz, CDCl3): δ 3.53 (t, 2H), 2.52 (t, 2H), 1.47 (s, 9H).

Workup

  1. additionpoured into reparatory funnel
  2. customThe layers separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0ac10be906c64ba88036aa4c0c54150b
Source dataset
uspto-grants-2015_06
Patent number
US09051320B1

Reaction notes

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