Ammonia → 1,3,5-Triethyl-4-(1H-imidazol-2-ylmethyl)-1H-pyrazole

HRID 254584Notes

Reaction equation

HRID 254584 reaction equation
C([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][C:14]1[C:15]([CH2:23][CH3:24])=[N:16][N:17]([CH2:21][CH3:22])[C:18]=1[CH2:19][CH3:20])C1C=CC=CC=1.[Na].N>>[CH2:21]([N:17]1[C:18]([CH2:19][CH3:20])=[C:14]([CH2:13][C:9]2[NH:8][CH:12]=[CH:11][N:10]=2)[C:15]([CH2:23][CH3:24])=[N:16]1)[CH3:22]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 589518964-(1-Benzyl-1H-imidazol-2-ylmethyl)-1,3,5-triethyl-1H-pyrazole

Product 1

HCID 589518391,3,5-Triethyl-4-(1H-imidazol-2-ylmethyl)-1H-pyrazole

Procedure

1,3,5-Triethyl-4-(1H-imidazol-2-ylmethyl)-1H-pyrazole was prepared from 4-(1-benzyl-1H-imidazol-2-ylmethyl)-1,3,5-triethyl-1H-pyrazole by debenzylation with sodium in liquid ammonia for 10 min. The blue reaction mixture was quenched by addition of solid ammonium chloride, the ammonia evaporated and the residue distributed between water and t-butyl methyl ether. The organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated. 1,3,5-Triethyl-4-(1H-imidazol-2-ylmethyl)-1H-pyrazole was obtained as light yellow viscous oil; MS (ISP): 233.0 ((M+H)+.).

Workup

  1. customThe blue reaction mixture
  2. customwas quenched by addition of solid ammonium chloride
  3. customthe ammonia evaporated
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-84efac272045442f8e800e3780470cc0
Source dataset
uspto-grants-2011_01
Patent number
US07875645B2

Reaction notes

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