Pyrrolidine → HCID 23337277, compound

HRID 902996Notes

Reaction equation

HRID 902996 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:6][C:7]([Cl:15])([Cl:14])[C:8]1[N:12]=[C:11](Cl)[S:10][N:9]=1>CCOCC>[Cl:6][C:7]([Cl:15])([Cl:14])[C:8]1[N:12]=[C:11]([N:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[S:10][N:9]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 799301,2,4-Thiadiazole, 5-chloro-3-(trichloromethyl)-

Product 1

HCID 23337277HCID 23337277, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To 14.2 grams (0.2 mole) pyrrolidine in 100 milliliters ether was added 23.8 grams (0.1 mole) 3-trichloromethyl-5-chloro-1,2,4-thiadiazole in 100 milliliters ether. The solution was refluxed with stirring for one hour after addition. Filtration to remove salt by-products yielded a clear filtrate which was concentrated on a steam bath to give 16.4 grams (60% molar yield) of white solid. Recrystallization from ligroin yielded a pure product (melting point 105.5°-107° C.). The structure was confirmed via infrared and elemental analysis. Analysis for C7H8N3Cl3S:

Workup

  1. temperatureThe solution was refluxed
  2. additionafter addition
  3. filtrationFiltration
  4. customto remove salt by-products
  5. customyielded a clear filtrate which
  6. concentrationwas concentrated on a steam bath
  7. customto give
  8. custom16.4 grams (60% molar yield) of white solid
  9. customRecrystallization from ligroin

Sources & evidence

ORD record
ord-4e7f432a75e4400c9d8e9ecf3130a98c
Source dataset
uspto-grants-1980_10
Patent number
US04226609

Reaction notes

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