Benzeneacetamide → Phenylacetyl isocyanate

HRID 2117072Notes

Reaction equation

HRID 2117072 reaction equation
[C:1]1([CH2:7][C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)[C:12](Cl)=[O:13]>ClC(Cl)C>[C:1]1([CH2:7][C:8]([N:10]=[C:12]=[O:13])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7680BenzeneacetamideHCID 65578Oxalyl chloride

Product 1

HCID 12259960Phenylacetyl isocyanate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a suspension of 2-phenylacetamide (68 mg, 0.5 mmol) in dichloroethane (2 mL) was added oxalyl chloride (0.175 mL, 2.0 mmol). The suspension dissolved quickly and a new suspension formed. LC/MS analysis of the reaction mixture after 5 min indicated none of the desired product had formed. The mixture was warmed to 80° C., LC/MS after 30 min indicated a small amount of product. The reaction was heated at 70° C. for 2 days and became mostly clear. LC/MS analysis indicated mostly product. The mixture was shaken and heated at 80° C. for another 4 h. Almost all of the yellow solid on the walls of the reaction vessel had dissolved. The mixture was concentrated in vacuo. The residue dissolved in dichloroethane (1.5 mL), concentrated, and redissolved in dichloroethane (2 mL). The resulting 0.25 M solution was used without further purification.

Workup

  1. dissolutionThe suspension dissolved quickly
  2. customa new suspension formed

Sources & evidence

ORD record
ord-92867bf0db094521bfdad40b874eac9b
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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