Triethylamine → Methyl 2-isocyanato-2-methylpropanoate

HRID 2306087Notes

Reaction equation

HRID 2306087 reaction equation
Cl.[NH2:2][C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.Cl[C:18](Cl)([O:20]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[N:2]([C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5])=[C:18]=[O:20]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 94429TriphosgeneHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 2769374Methyl 2-isocyanato-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the methyl 2-amino-2-methylpropanoate hydrochloride(65.5 g) in THF (650 mL) was treated with triethylamine (60 mL), heated to reflux, stirred for 30 minutes, cooled to room temperature, treated dropwise with a solution of triphosgene (43.2 g) in THF (250 mL) over 5 minutes, heated to reflux, stirred for 4 hours, cooled to 15° C., treated with triethylamine (120 mL) over 7 minutes, heated to reflux, stirred for 40 minutes, cooled to room temperature, and filtered. The solid was washed with THF and the filtrate was collected to provide a solution of methyl 2-isocyanato-2-methylpropanoate in THF.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureheated
  4. temperatureto reflux
  5. stirringstirred for 4 hours
  6. temperaturecooled to 15° C.
  7. temperatureheated
  8. temperatureto reflux
  9. stirringstirred for 40 minutes
  10. temperaturecooled to room temperature
  11. filtrationfiltered
  12. washThe solid was washed with THF
  13. customthe filtrate was collected

Sources & evidence

ORD record
ord-b86f3c67b9ef45c0a7dd779ce2a12af8
Source dataset
uspto-grants-2002_08
Patent number
US06441189B1

Reaction notes

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