Pyrrolidine → HCID 19605458, compound

HRID 1603561Notes

Reaction equation

HRID 1603561 reaction equation
Cl[C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4]([Cl:18])[N:3]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>O1CCOCC1>[Cl:18][C:4]1[CH:5]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:7]=[C:2]([N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 19605512HCID 19605512, compound

Product 1

HCID 19605458HCID 19605458, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

16.8 g (0.0554 Mol) 4-(2,6-dichloro-pyridine-4-sulfonyl)-phenylamine were dissolved in dioxane (165 ml), 23.0 ml (0.2753 Mol) pyrrolidine were added at ambiente temperature and stirred for 1.5 h. The reaction mixture was then poured onto water (600 ml), stirred for 1 h and filtered. The residue on the filter was washed with water (150 ml), dissolved in tetrahydrofuran (250 ml) and treated with Na2SO4 (20.0 g) and Norit-SX-1 (1.7 g). After filtration the residue on the filter was washed with tetrahydrofuran (100 ml) and subsequently dried in a high vacuum. It was obtained 18.4 g (98%) 4-(2-chloro-6-pyrrolidin-1-yl-pyridine-4-sulfonyl)-phenylamine as a bright yellow powder; mp.: 225-226° C.

Workup

  1. additionThe reaction mixture was then poured onto water (600 ml)
  2. stirringstirred for 1 h
  3. filtrationfiltered
  4. washThe residue on the filter was washed with water (150 ml)
  5. dissolutiondissolved in tetrahydrofuran (250 ml)
  6. additiontreated with Na2SO4 (20.0 g) and Norit-SX-1 (1.7 g)
  7. filtrationAfter filtration the residue on the filter
  8. washwas washed with tetrahydrofuran (100 ml)
  9. customsubsequently dried in a high vacuum

Sources & evidence

ORD record
ord-15dbf2b84a534bdc91478739731a5907
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

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