Triphenylphosphine → HCID 131718327, compound

HRID 1974770Notes

Reaction equation

HRID 1974770 reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([Cl:7])[N:6]=1.[NH2:8][C:9]([CH3:13])([CH3:12])[C:10]#[CH:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Pd+2].[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I.C(N(CC)CC)C>[NH2:8][C:9]([CH3:13])([CH3:12])[C:10]#[C:11][C:2]1[S:3][CH:4]=[C:5]([Cl:7])[N:6]=1

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 763193-Butyn-2-amine, 2-methyl-HCID 123331552,4-Dichlorothiazole

Product 1

HCID 131718327HCID 131718327, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 84124Bis(triphenylphosphine)palladium chlorideCatalystHCID 8471TriethylamineSolvent

Procedure

46.2 g (0.30 mol) of 2,4-dichloro-thiazole and 24.9 g (0.30 mol) of 3-amino-3, 3-dimethyl-1-propine are introduced into 300 ml of triethylamine. After 2.1 g (0.003 mol) of palladium(II)-bis(triphenylphosphine) dichloride, 2.28 g (0.012 mol) of copper(I) iodide and 3.2 g (0.012 mol) of triphenylphosphine have been added, the reaction mixture is refluxed for 19 hours. It is then filtered, the filtrate is concentrated under a water-pump vacuum, the residue is taken up in chloroform, and the mixture is extracted by shaking with dilute aqueous hydrochloric acid. The aqueous phase is rendered alkaline using sodium hydroxide solution and extracted several times by shaking with chloroform. After the organic phase has been dried over sodium sulphate, it is concentrated and the residue is chromatographed over silica gel (mobile phase: methylene chloride/methanol (96/4). 15.6 g (26 % of theory) of 3-amino-3, 3-dimethyl-1-(4-chloro-thiazol-2-yl)-1-propine with a melting point of 62-640° C. are obtained.

Workup

  1. temperaturethe reaction mixture is refluxed for 19 hours
  2. filtrationIt is then filtered
  3. concentrationthe filtrate is concentrated under a water-pump vacuum
  4. extractionthe mixture is extracted
  5. extractionextracted several times
  6. stirringby shaking with chloroform
  7. dry with materialAfter the organic phase has been dried over sodium sulphate, it
  8. concentrationis concentrated
  9. customthe residue is chromatographed over silica gel (mobile phase

Sources & evidence

ORD record
ord-0539bdd627644150927a51d100b39f18
Source dataset
uspto-grants-1994_02
Patent number
US05283363

Reaction notes

Loading…