Phenylacetyl chloride → N-(Cyanomethyl)-2-phenylethanimidic acid

HRID 2231839Notes

Reaction equation

HRID 2231839 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[N:5].C(N(CC)CC)C.[C:13]1([CH2:19][C:20](Cl)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCCCCC>C(Cl)(Cl)Cl>[C:4]([CH2:3][NH:2][C:20](=[O:21])[CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)#[N:5]

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8058HexaneHCID 8471TriethylamineHCID 11491918Aminoacetonitrile hydrochloride

Product 1

HCID 231599N-(Cyanomethyl)-2-phenylethanimidic acid

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To aminoacetonitrile hydrochloride and 40 g (0.4 moles) triethylamine in 300 ml chloroform which was then cooled in an ice bath, the acid chloride from step (a) in 50 ml chloroform was dropped in over 60 minutes. The reaction mixture was washed three times with 200 ml water, dried over magnesium sulfate and stripped to give an oil. The oil was rubbed with 50 ml hexane and immediately solidified to give 30.4 g of beige solids, melting point 87° C. to 91° C.

Workup

  1. washThe reaction mixture was washed three times with 200 ml water
  2. dry with materialdried over magnesium sulfate
  3. customto give an oil

Sources & evidence

ORD record
ord-b7cfd4dd3d6b4db4ab0f209974ddf004
Source dataset
uspto-grants-1988_11
Patent number
US04785019

Reaction notes

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