Triphenylphosphine → 6-(2-Acetylthioethyl)-2-pyridylamine
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[NH2:32][C:33]1[N:38]=[C:37]([CH2:39][CH2:40]O)[CH:36]=[CH:35][CH:34]=1.[C:42]([OH:45])(=[S:44])[CH3:43]>O1CCCC1>[C:42]([S:44][CH2:40][CH2:39][C:37]1[N:38]=[C:33]([NH2:32])[CH:34]=[CH:35][CH:36]=1)(=[O:45])[CH3:43]Participants
6
Procedure
Triphenyl phosphine (2.36 g) was dissolved in tetrahydrofuran (40 ml). To the solution was added, at −20° C., diethyl azodicarboxylate (1.56 g). The mixture was stirred for 5 minutes, to which was added a solution of 2-(6-amino-2-pyridyl)ethanol (0.62 g) in tetrahydrofuran (2 ml). The mixture was stirred for one minutes, to which was added thioacetic acid (0.64 ml), followed by stirring for 4 hours at 25° C. The reaction mixture was concentrated under reduced pressure. The concentrate was purified by means of a column chromatography (carrier: silica gel, 120 g, developing solvent: ethyl acetate-hexane, 2:1) to give the title compound (0.56 g), m.p.55-59° C.
Workup
- additionTo the solution was added, at −20° C.
- stirringThe mixture was stirred for one minutes, to which
- stirringby stirring for 4 hours at 25° C
- concentrationThe reaction mixture was concentrated under reduced pressure
- customThe concentrate was purified by means of a column chromatography (carrier: silica gel, 120 g, developing solvent: ethyl acetate-hexane, 2:1)
Sources & evidence
- ORD record
- ord-a071540fdb2843128c986b1d4ff25993
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06174877B1
Reaction notes
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