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

HRID 29798

Reaction equation

HRID 29798 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 at 0° C. to a solution of 4.87 g (28 mmol) 5-methyl-3-p-tolyl-[1,2,4]triazole in 40 mL of DMPU. The reaction mixture is heated to ambient temperature and then stirred for one hour. 9.35 g (42 mmol) tert-butyl (3-chloro-1,1-dimethyl-propyl)-carbamate and 1.87 g (5 mmol) tetrabutylammonium iodide are added and the mixture is stirred overnight at ambient temperature and then for 2 hours at 80° C. The mixture 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. Yield: 2.97 g (30%); mass spectroscopy [M+H]+=359.

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-9abc96cf68074ffdb19d2362b2f5e482
Source dataset
uspto-grants-2008_09
Patent number
US07423036B2

Linked notes

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