Diethyl Ether → 2-Ethoxycarbonyl-1,1-dimethylethylisocyanate

HRID 2309680Notes

Reaction equation

HRID 2309680 reaction equation
Cl[C:2](OC(Cl)(Cl)Cl)=[O:3].[CH2:9]([O:11][C:12](=[O:18])[CH2:13][C:14]([NH2:17])([CH3:16])[CH3:15])[CH3:10].C(N(CC)CC)C.CCOCC>C(Cl)Cl>[CH2:9]([O:11][C:12]([CH2:13][C:14]([N:17]=[C:2]=[O:3])([CH3:16])[CH3:15])=[O:18])[CH3:10]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 10426DiphosgeneHCID 11480520Ethyl 3-amino-3-methylbutanoate

Product 1

HCID 139389532-Ethoxycarbonyl-1,1-dimethylethylisocyanateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of trichloromethyl chloroformate (4.1 g) in methylene chloride (15 ml) is slowly added to a stirred mixture of ethyl-3-amino-3-methylbutanoate (3 g), triethylamine (6.6 g) and methylene chloride (30 ml) at 5° C. The mixture is stirred overnight at room temperature, refluxed for 3 hours, cooled and anhydrous ether added thereto. The precipitated triethylamine hydrochloride is filtered and the filtrate evaporated to yield 2-ethoxycarbonyl-1,1-dimethylethylisocyanate as an oil (3.5 g).

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturecooled
  3. filtrationThe precipitated triethylamine hydrochloride is filtered
  4. customthe filtrate evaporated

Sources & evidence

ORD record
ord-27d8fd05bfee402ca80ceb4d43829dd6
Source dataset
uspto-grants-1987_09
Patent number
US04696927

Reaction notes

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