Ethyl chloroacetate → HCID 85821330, compound

HRID 426893Notes

Reaction equation

HRID 426893 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Cl:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C)C=O.C(Cl)(Cl)Cl>[Cl-:13].[Cl-:13].[CH2:18]([O:17][C:15]([CH2:14][N+:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][N+:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1)=[O:16])[CH3:19]

Participants

5

Reactant 2

HCID 7751Ethyl chloroacetate2×HCID 111074,4'-Bipyridine

Product 1

HCID 85821330HCID 85821330, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

4,4'-Bipyridyl (156 g) was heated with ethyl chloroacetate (245 g) in dry dimethylformamide (400 ml) to 90°- 100° C. After 2 hours a further quantity of ethyl chloroacetate (123 g) was added and the mixture heated a further 2.5 hours at 120° C. The solution was cooled, diluted with chloroform (400 ml), stirred a short time at 0° C., and the solid collected, washed with chloroform and dried. The 1,1'-di-ethoxycarbonylmethyl-4,4'-bipyridylium dichloride so obtained (340 g) was dissolved in concentrated hydrochloric acid and heated under reflux for 3 hours. The mixture was cooled to 0° C., acetone (200 ml) slowly added, and the grey solid collected, washed with acetone, and dried, giving 1,1'-dicarboxymethyl-4,4'-bipyridylium dichloride.

Workup

  1. temperatureThe solution was cooled
  2. customthe solid collected
  3. washwashed with chloroform
  4. customdried

Sources & evidence

ORD record
ord-1e9050bd359a4a1fbc56a075e3d35efc
Source dataset
uspto-grants-1979_10
Patent number
US04171967

Reaction notes

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