Ammonia → HCID 16067174, compound

HRID 2109277Notes

Reaction equation

HRID 2109277 reaction equation
[CH2:1]([O:8][CH2:9][C:10]([CH3:15])([CH3:14])[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[N:18](CC)CC.ClC(OCC)=O.N>C(Cl)(Cl)Cl>[CH2:1]([O:8][CH2:9][C:10]([CH3:15])([CH3:14])[C:11]([NH2:18])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 134782883-(Benzyloxy)-2,2-dimethylpropanoic acid

Product 1

HCID 16067174HCID 16067174, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 0° C. solution of 2.4 g (11.4 mmol) of 3-benzyloxy-2,2-dimethyl-propionic acid and 1.65 ml (11.5 mmol) of Et3N in 80 mL of chloroform was added 1.04 mL (11.5 mmol) of ethyl chloroformate. After stirring for 15 min, NH3 gas was passed through the solution for 5 minutes. The resulting suspension was removed from the ice bath and allowed to stir overnight. The suspension was filtered and the filtrate was concentrated to near dryness. The resulting residue was crystallized from benzene/hexanes (16 mL/40 mL) mixture to provide 2.3 g of 3-benzyloxy-2,2-dimethyl-propionamide.

Workup

  1. customThe resulting suspension was removed from the ice bath
  2. stirringto stir overnight
  3. filtrationThe suspension was filtered
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was crystallized from benzene/hexanes (16 mL/40 mL) mixture

Sources & evidence

ORD record
ord-07fa800be33c4f35a6835dad239ac988
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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