Pyridine → N-(3-Amino-4,6-dichlorophenyl)-gamma-chlorobutyramide

HRID 1706607Notes

Reaction equation

HRID 1706607 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5](Cl)=[O:6].[NH2:8][C:9]1[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[C:11]([NH2:17])[CH:10]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl>[NH2:8][C:9]1[CH:10]=[C:11]([NH:17][C:5](=[O:6])[CH2:4][CH2:3][CH2:2][Cl:1])[C:12]([Cl:16])=[CH:13][C:14]=1[Cl:15]

Participants

5

Reactant 3

HCID 1049PyridineHCID 783704-Chlorobutyryl chlorideHCID 33728694,6-Dichlorobenzene-1,3-diamine

Product 1

HCID 13062307N-(3-Amino-4,6-dichlorophenyl)-gamma-chlorobutyramide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

14.1 g (0.10 mol) of γ-chlorobutyryl chloride in 50 ml of chloroform are added dropwise in the course of 1 hour, at 10°-15° C., to a solution of 17.7 g (0.10 mol) of 1,3-diamino-4,6-dichlorobenzene and 8.7 g (0.11 mol) of pyridine in 500 ml of chloroform. The mixture is then stirred for 2 hours at room temperature, the solution is washed with water and filtered through 40 g of silica gel and the filtrate is concentrated. The resulting product is recrystallised from hexane/toluene. Yield: 13.5 g; melting point 125°-128° C.

Workup

  1. washthe solution is washed with water
  2. filtrationfiltered through 40 g of silica gel
  3. concentrationthe filtrate is concentrated
  4. customThe resulting product is recrystallised from hexane/toluene

Sources & evidence

ORD record
ord-e97ec65ee8eb447ea4ca8701f0bfb5c0
Source dataset
uspto-grants-1980_06
Patent number
US04208202

Reaction notes

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