Water → Tert-butyl [1,1-dimethyl-3-(5-methyl-3-p-tolyl-[1,2,4]triazol-1-yl)-propyl]-carbamate

HRID 1787849Notes

Reaction equation

HRID 1787849 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:8][N:7]=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[N:5]=1.Cl[CH2:17][CH2:18][C:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:21])[CH3:20].O>CN1C(=O)N(C)CCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:21][C:19]([NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:20])[CH2:18][CH2:17][N:8]1[C:4]([CH3:3])=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[N:7]1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 431667765-Methyl-3-(4-methylphenyl)-1H-1,2,4-triazoleHCID 57429079tert-butyl N-(4-chloro-2-methylbutan-2-yl)carbamate

Product 1

HCID 69538809Tert-butyl [1,1-dimethyl-3-(5-methyl-3-p-tolyl-[1,2,4]triazol-1-yl)-propyl]-carbamate

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

1.35 g (34 mmol, 60%) sodium hydride are added to a solution of 4.87 g (28 mmol) of 5-methyl-3-p-tolyl-[1,2,4]triazole in 40 mL DMPU at 0° C. The reaction mixture is heated to ambient temperature and then stirred for one hour. 9.35 g (42 mmol) of tert.butyl (3-chloro-1,1-dimethyl-propyl)-carbamate and 1.87 g (5 mmol) of tetrabutylammonium iodide are added and the mixture is stirred overnight at ambient temperature and then for 2 hours at 80° C. It is combined with water and ethyl acetate, the aqueous phase is separated off and extracted with ethyl acetate. The combined organic phases are washed with water and sodium chloride solution, dried with sodium sulphate and evaporated down. The residue is purified by column chromatography (silica gel; petroleum ether/ethyl acetate=1.1). Oil.

Workup

  1. stirringthe mixture is stirred overnight at ambient temperature
  2. waitfor 2 hours at 80° C
  3. customthe aqueous phase is separated off
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases are washed with water and sodium chloride solution
  6. dry with materialdried with sodium sulphate
  7. customevaporated down
  8. customThe residue is purified by column chromatography (silica gel; petroleum ether/ethyl acetate=1.1)

Sources & evidence

ORD record
ord-a9735160f2dc458d91fffa7416777b23
Source dataset
uspto-grants-2009_03
Patent number
US07511067B2

Reaction notes

Loading…