Pyridine → HCID 12297777, compound

HRID 1731790Notes

Reaction equation

HRID 1731790 reaction equation
[S:1]([Cl:3])Cl.N1C=CC=CC=1.[CH2:10]([NH:13][CH2:14][CH2:15][CH3:16])[CH2:11][CH3:12]>ClCCl>[CH2:10]([N:13]([CH2:14][CH2:15][CH3:16])[S:1][Cl:3])[CH2:11][CH3:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8902DipropylamineHCID 25353Sulfur dichloride

Product 1

HCID 12297777HCID 12297777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

22.7 g of sulphur dichloride in 100 ml of dichloromethane was cooled to -5° C. and a solution of 17.4 g of pyridine in 50 ml of dichloromethane was added, over 30 minutes, while the temperature was maintained between -5° and 0° C. The resulting solution was stirred for 15 minutes and a solution of 20.2 g of di(n-propyl)amine dissolved in 50 ml of dichloromethane was added, over 30 minutes, while the temperature was maintained between -5° and 0° C. The resulting solution was stirred for 2 hours, while the temperature was allowed to rise to ambient. The solution was filtered and the solvent was evaporated. 150 ml of diethyl ether was added, the resulting solution was filtered, and the filtrate evaporated. Distillation of the residue gave di(n-propyl)aminosulphenyl chloride (38B), b.p.: 94°-5° C. at 15 Torr.

Workup

  1. temperaturewas maintained between -5° and 0° C
  2. additionwas added, over 30 minutes, while the temperature
  3. temperaturewas maintained between -5° and 0° C
  4. stirringThe resulting solution was stirred for 2 hours, while the temperature
  5. filtrationThe solution was filtered
  6. customthe solvent was evaporated
  7. addition150 ml of diethyl ether was added
  8. filtrationthe resulting solution was filtered
  9. customthe filtrate evaporated
  10. distillationDistillation of the residue

Sources & evidence

ORD record
ord-9681c6afb1e14b578feae6c03567b0db
Source dataset
uspto-grants-1986_11
Patent number
US04623658

Reaction notes

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