Ammonium Acetate → HCID 59644531, compound

HRID 2251995Notes

Reaction equation

HRID 2251995 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]([C:20]2[C:21]([CH2:32][CH:33]=O)=[N:22][O:23][C:24]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])=O)[N:9]=[N:8]1.C([O-])(=O)C.[NH4+:48]>C(O)(=O)C>[F:43][C:2]([F:1])([F:42])[C:3]1[CH:4]=[C:5]([CH:35]=[C:36]([C:38]([F:40])([F:39])[F:41])[CH:37]=1)[CH2:6][N:7]1[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:10]([C:18]2[C:20]3=[C:24]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[Cl:31])[O:23][N:22]=[C:21]3[CH:32]=[CH:33][N:48]=2)[N:9]=[N:8]1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 10290086HCID 10290086, compound

Product 1

HCID 59644531HCID 59644531, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

Combine [4-[1-(3,5-bis-trifluoromethyl-benzyl)-5-phenyl-1H-[1,2,3]triazole-4-carbonyl]-5-(2-chloro-phenyl)-isoxazol-3-yl]-acetaldehyde (0.401 g, 0.65 mmol) and acetic acid (4.5 mL), add ammonium acetate (0.25 g, 3.2 mmol) and stir at 65° C. for 90 minutes. Concentrate, neutralize with saturated aqeous NaHCO3, extract with ether, dry over MgSO4, filter and concentrate under vacuum. Purify on chromatotron, using EtOAc/Hexane (10%-85%) to give the title compound: Exact mass 599.1, MS (IS) 600.1 (M+1), 1H NMR (CDCl3): δ 8.15 (d, J=6.6 Hz, 1H), 7.85 (s, 1H), 7.60 (m, 1H), 7.52-7.38 (m, 8H), 7.17 (m, 2H), 5.54 (s, 2H).

Workup

  1. concentrationConcentrate
  2. extractionextract with ether
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate under vacuum
  6. customPurify on chromatotron

Sources & evidence

ORD record
ord-19d1dc08e585483c8c18e229f65f6626
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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