Sulfuric Acid → 1-Benzyl-5-isovaleramido-4-isovalerylcarbamoyl-1,2,3-triazole

HRID 1288295Notes

Reaction equation

HRID 1288295 reaction equation
S(=O)(=O)(O)O.[NH2:6][C:7]1[N:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:10]=[N:9][C:8]=1[C:19](=[O:21])[NH2:20].[C:22](Cl)(=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25]>>[CH2:12]([N:11]1[C:7]([NH:6][C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])=[C:8]([C:19](=[O:21])[NH:20][C:22](=[O:27])[CH2:23][CH:24]([CH3:26])[CH3:25])[N:9]=[N:10]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 66054Isovaleryl chlorideHCID 2254355-Amino-1-benzyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 215043541-Benzyl-5-isovaleramido-4-isovalerylcarbamoyl-1,2,3-triazole

Procedure

Concentrated sulphuric acid (7.5 ml.) was added dropwise, under anhydrous conditions, to an ice-cooled, stirred suspension of 5-amino-1-benzyl-4-carbamoyl-1,2,3-triazole (10.85 g.; prepared as described by J. R. E. Hoover and A. R. Day, J.Amer.Chem.Soc., 1956, 78, 5832) in isovaleryl chloride (50 ml.), and the mixture was then stirred at room temperature overnight. The resulting solution was poured into ice-water, and the precipitated solid filtered off, stirred well with water, again filtered off, and dried, to give 1-benzyl-5-isovaleramido-4-isovalerylcarbamoyl-1,2,3-triazole (16.4 g.), m.p. 125°-128° C. An aliquot was recrystallised from di-isopropyl ether to give pure 1benzyl-5-isovaleramido-4-isovalerylcarbamoyl-1,2,3-triazole, m.p. 130°-131° C.

Workup

  1. temperaturecooled
  2. customprepared
  3. filtrationthe precipitated solid filtered off
  4. stirringstirred well with water
  5. filtrationagain filtered off
  6. customdried

Sources & evidence

ORD record
ord-0d110f42e5c64db6a7c4174244879e04
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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