Pyridine → Bis(ethoxycarbonylmethyl)aminosulfenyl Chloride

HRID 904998Notes

Reaction equation

HRID 904998 reaction equation
[S:1]([Cl:3])Cl.N1C=CC=[CH:6][CH:5]=1.[NH:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][C:12]([O-:14])=[O:13]>C(Cl)(Cl)(Cl)Cl>[CH2:19]([O:18][C:16]([CH2:15][N:10]([CH2:11][C:12]([O:14][CH2:5][CH3:6])=[O:13])[S:1][Cl:3])=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 25353Sulfur dichlorideHCID 18321666Ethyl iminodiacetate

Product 1

HCID 13135109Bis(ethoxycarbonylmethyl)aminosulfenyl Chloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2.1 g (0.02 mole) of sulfur dichloride was dissolved in 35 ml of carbon tetrachloride, and 1.6 g (0.02 mole) of pyridine was dropwise added to the resulting solution at 0° to 5° C. After completion of the dropwise addition, 3.8 g (0.02 mole) of ethyl iminodiacetate was further dropwise added thereto at 10° to 20° C., and the resulting mixture was stirred for one hour at the same temperature. After completion of the reaction, crystals were filtered off, and the mother liquor was concentrated under reduced pressure to obtain an oily product. Yield: 5.0 g (98%).

Workup

  1. additionwas further dropwise added
  2. customAfter completion of the reaction, crystals
  3. filtrationwere filtered off
  4. concentrationthe mother liquor was concentrated under reduced pressure
  5. customto obtain an oily product

Sources & evidence

ORD record
ord-a5f692367d50414c9e9f644066e05bf6
Source dataset
uspto-grants-1983_12
Patent number
US04421693

Reaction notes

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