Hydrochloric Acid → 2-(2-Dodecyl-2H-tetrazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

HRID 264046

Reaction equation

HRID 264046 reaction equation
[CH2:1]([N:13]1[N:17]=[N:16][C:15]([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([OH:21])=O)=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:40][O:41][C:42]1[CH:48]=[C:47]([O:49][CH3:50])[CH:46]=[C:45]([O:51][CH3:52])[C:43]=1[NH2:44].Cl>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:13]1[N:17]=[N:16][C:15]([CH:18]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:19]([NH:44][C:43]2[C:45]([O:51][CH3:52])=[CH:46][C:47]([O:49][CH3:50])=[CH:48][C:42]=2[O:41][CH3:40])=[O:21])=[N:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 842712,4,6-TrimethoxyanilineHCID 10523337alpha-(2-Dodecyl-2H-5-tetrazolyl)phenylacetic acid

Product 1

HCID 98934132-(2-Dodecyl-2H-tetrazol-5-yl)-2-phenyl-N-(2,4,6-trimethoxy-phenyl)-acetamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The compound obtained in (d) above (6.58 g; 17.6 mmoles) was dissolved in tetrahydrofuran (50 mL), treated with carbonyldiimidazole (3.1 g; 19.1 mmoles), and stirred for 1 hour at room temperature under an atmosphere of N2. A solution of 2,4,6-trimethoxyaniline (3.2 g; 17.6 mmoles/50 mL THF) was then added in one portion and the solution was stirred at room temperature for overnight. Ethyl acetate (150 mL) was then added as well as aqueous HCl (1N). The layers were separated and the organic portion was washed with NaOH (1N), brine, and then dried over MgSO4. The drying agent was filtered and the filtrate concentrated in vacuo leaving a lavender colored solid which was purified by silica gel chromatography using chloroform (95%)/methanol (5%) as the eluent. Yield: 6.7 g (70%), mp 119°-120° C.

Workup

  1. stirringthe solution was stirred at room temperature for overnight
  2. customThe layers were separated
  3. washthe organic portion was washed with NaOH (1N), brine
  4. dry with materialdried over MgSO4
  5. filtrationThe drying agent was filtered
  6. concentrationthe filtrate concentrated in vacuo
  7. customleaving a lavender colored solid which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-cef04950952e48a2aa73a44402945d2a
Source dataset
uspto-grants-1997_07
Patent number
US05646170

Linked notes

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