Hydrazine hydrate (1:1) → HCID 67091898, compound

HRID 2074111Notes

Reaction equation

HRID 2074111 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=O)[CH2:10][C:11]([C:13]2[N:14]=[CH:15][N:16]([C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:17]=2)=O)=[CH:4][CH:3]=1.[NH2:38][NH2:39].O>CCO.CC(O)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[NH:39][N:38]=[C:11]([C:13]3[N:14]=[CH:15][N:16]([C:18]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=3)[CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 67092210HCID 67092210, compound

Product 1

HCID 67091898HCID 67091898, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 18476134Acetic acid ethanolSolvent

Procedure

To a mixture of 4-(4-fluorophenyl)-1-(1-trityl-1H-imidazol-4-yl)butane-1,3-dione (80 g, 0.165 mol) and anhydrous EtOH/AcOH (400 mL/100 mL) was added NH2NH2.H2O (80 mL, 0.96 mol) dropwise at 0° C. After the addition, the mixture was stirred at RT overnight. The solvent mixture was evaporated, the residue washed with anhydrous Et2O (4×250 mL) and the resulting precipitate was dried in oven to yield the title compound (58.8 g, 73.0%) as a yellow solid.

Workup

  1. additionAfter the addition
  2. customThe solvent mixture was evaporated
  3. washthe residue washed with anhydrous Et2O (4×250 mL)
  4. customthe resulting precipitate was dried in oven

Sources & evidence

ORD record
ord-ccb204f5401f4c1caacf17b6d94df235
Source dataset
uspto-grants-2011_04
Patent number
US07919488B2

Reaction notes

Loading…