Hydroxyamine hydrochloride → HCID 178431166, compound

HRID 231254Notes

Reaction equation

HRID 231254 reaction equation
[CH3:1][C:2]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[NH:22][N:21]=[N:20][N:19]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=O.Cl.[NH2:24][OH:25].C([O-])(=O)C.[Na+]>C(O)C>[CH3:1][C:2]1([CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][C:18]3[NH:22][N:21]=[N:20][N:19]=3)=[CH:13][CH:12]=2)[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[N:24][OH:25]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 178431167HCID 178431167, compound

Product 1

HCID 178431166HCID 178431166, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-2-[[4-(1H-tetrazol-5-yl-methyl)phenoxy]-methyl]cyclohexanone (0.79 g, prepared in Example 3), hydroxylamine hydrochloride (0.22 g), sodium acetate (0.26 g) and ethanol (absolute, 20 ml) were combined and heated to reflux for 4 hours. The ethanol was removed in vacuo. The residue was partitioned between ethyl acetate and 10% HCl solution. The organic phase was washed with saturated aqueous NaCl solution, dried over MgSO4 and concentrated on the rotary evaporator. The product was triturated with dichloromethane-diethyl ether mixture to afford 0.47 g of white solid, mp 153°-156° C. Analytical HPLC showed the product was 97.7% pure.

Workup

  1. temperatureheated
  2. temperatureto reflux for 4 hours
  3. customThe ethanol was removed in vacuo
  4. customThe residue was partitioned between ethyl acetate and 10% HCl solution
  5. washThe organic phase was washed with saturated aqueous NaCl solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated on the rotary evaporator
  8. customThe product was triturated with dichloromethane-diethyl ether mixture

Sources & evidence

ORD record
ord-392e2180a1c24ec48e9b31eb068bd426
Source dataset
uspto-grants-1989_07
Patent number
US04845231

Reaction notes

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