Ammonia → HCID 58951917, compound

HRID 1694816Notes

Reaction equation

HRID 1694816 reaction equation
C([N:8]1[C:12]([CH2:13][C:14]2[C:15]([CH2:23][CH3:24])=[N:16][N:17]([CH2:21][CH3:22])[C:18]=2[CH2:19][CH3:20])=[CH:11][N:10]=[CH:9]1)C1C=CC=CC=1.[Na].N>>[CH2:21]([N:17]1[C:18]([CH2:19][CH3:20])=[C:14]([CH2:13][C:12]2[NH:8][CH:9]=[N:10][CH:11]=2)[C:15]([CH2:23][CH3:24])=[N:16]1)[CH3:22]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 58951937HCID 58951937, compound

Product 1

HCID 58951917HCID 58951917, compound

Procedure

1,3,5-Triethyl-4-(3H-imidazol-4-ylmethyl)-1H-pyrazole was prepared from 4-(3-benzyl-3H-imidazol-4-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-(3H-imidazol-4-ylmethyl)-1H-pyrazole was obtained as light yellow solid; 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-28d1fdf0710441c7bc5715098ca4c5ba
Source dataset
uspto-grants-2012_04
Patent number
US08158668B2

Reaction notes

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