Triethylamine → HCID 10714679, compound

HRID 1461001Notes

Reaction equation

HRID 1461001 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1.[CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[C:18]=1[N:26]=[C:27]=[O:28])([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:24])[CH3:25])[C:18]=1[NH:26][C:27]([NH:1][C:2]1[N:3]=[N:4][N:5]([CH2:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:6]=1)=[O:28])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 922592,6-Diisopropylphenyl isocyanateHCID 5624012-(Phenylmethyl)-2H-tetrazol-5-amine

Product 1

HCID 10714679HCID 10714679, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-benzyltetrazole (1.55 g, 8.84 mmol) was dissolved in 20 mL methylene chloride after which 2,6-diisopropylphenyl isocyanate (2.25 mL, 10.6 mmol) and 1.5 mL triethylamine was added. The mixture was stirred at room temperature for 4 days then quenched with 5 mL 2N sulfuric acid and extracted with 50 mL ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium carbonate, dried over magnesium sulfate, filtered, and evaporated, leaving a white solid which was recrystallized from ethyl acetate/ether to give the title compound, m.p. 180-181° C.

Workup

  1. additionwas added
  2. customthen quenched with 5 mL 2N sulfuric acid
  3. extractionextracted with 50 mL ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materiala saturated aqueous solution of sodium carbonate, dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customleaving a white solid which
  9. customwas recrystallized from ethyl acetate/ether

Sources & evidence

ORD record
ord-6f1b3eaf89ac48d9bf1d87c42505f1d5
Source dataset
uspto-grants-1991_12
Patent number
US05073565

Reaction notes

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