Triethylamine → 1434655-18-1

HRID 870488Notes

Reaction equation

HRID 870488 reaction equation
[NH2:1][C:2]([CH3:11])([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[C:12](OC(Cl)(Cl)Cl)(OC(Cl)(Cl)Cl)=[O:13].C(N(CC)CC)C>ClCCl>[N:1]([C:2]([CH3:11])([CH3:10])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[C:12]=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 7019940tert-Butyl 2-methylalaninate

Product 1

HCID 895572641434655-18-1Yield 298.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100-mL 3-necked round-bottom flask was placed a solution of tert-butyl 2-amino-2-methylpropanoate (1.2 g, 7.54 mmol, 1.00 equiv) in dichloromethane (20 mL). This was followed by the addition of ditrichloromethyl carbonate (750 mg, 2.53 mmol, 0.34 equiv), in portions at 0° C. After 30 min, triethylamine (2.3 g, 22.73 mmol, 3.02 equiv) was added dropwise with stirring. The resulting solution was stirred for 5 h at room temperature and then concentrated under vacuum. The residue was diluted with 20 mL of ethyl ether. The solids were filtered out. The filtrate was concentrated under vacuum. Purification afforded 1.4 g (crude) of tert-butyl 2-isocyanato-2-methylpropanoate (110.2) as a yellow oil.

Workup

  1. customInto a 100-mL 3-necked round-bottom flask was placed
  2. stirringThe resulting solution was stirred for 5 h at room temperature
  3. concentrationconcentrated under vacuum
  4. additionThe residue was diluted with 20 mL of ethyl ether
  5. filtrationThe solids were filtered out
  6. concentrationThe filtrate was concentrated under vacuum
  7. customPurification

Sources & evidence

ORD record
ord-8686c9ac0d65419fab27d6b5750e4036
Source dataset
uspto-grants-2015_03
Patent number
US08969557B2

Reaction notes

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