Acetic Anhydride → N-acetyl-2,3-dichlorophenacylamine

HRID 1194113Notes

Reaction equation

HRID 1194113 reaction equation
[Cl:1][C:2]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([C:6]#[N:7])=[O:5].[H][H].[C:15](OC(=O)C)(=[O:17])[CH3:16]>C(O)(=O)C.O=[Pt]=O>[C:15]([NH:7][CH2:6][C:4]([C:3]1[CH:8]=[CH:9][CH:10]=[C:11]([Cl:12])[C:2]=1[Cl:1])=[O:5])(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 2735968(2,3-Dichlorophenyl)oxoacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 22151844N-acetyl-2,3-dichlorophenacylamine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

150 g of 2,3-dichlorobenzoyl cyanide are hydrogenated with elemental hydrogen under normal pressure at 70° C. in 1.5 l of glacial acetic acid and 84.15 g of acetic anhydride over 5 g of PtO2. After absorption of 112% of the calculated amount of hydrogen (time taken: c. 5 hours), the hydrogenation is discontinued, the reaction mixture is filtered and the filtrae is concentrated by evaporation. The residual yellow oil is crystallised by addition of hexane/diethyl ether. The crystalline product is isolated by filtration and dried. M.p. 107°-109° C. IR (solid/KBr) in cm-1 : 3300 (NH); 1735 (CO); 1650 (CO). 1H-NMR (CDCl3) in ppm: 2.08 (s, 3H); 4.55 (d, 2H); 6.2-6.6 (broad s, 1H); 7.25 (m, 3H).

Workup

  1. customAfter absorption of 112% of the calculated amount of hydrogen (time taken: c. 5 hours)
  2. filtrationthe reaction mixture is filtered
  3. concentrationthe filtrae is concentrated by evaporation
  4. customThe residual yellow oil is crystallised by addition of hexane/diethyl ether
  5. customThe crystalline product is isolated by filtration
  6. customdried

Sources & evidence

ORD record
ord-af0729974643473db171a11ba680ea09
Source dataset
uspto-grants-1989_03
Patent number
US04812580

Reaction notes

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