Hydroxyamine hydrochloride → HCID 86656395, compound

HRID 1948509Notes

Reaction equation

HRID 1948509 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:10]=[C:9]([CH:11]=[CH2:12])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].C(=O)(O)[O-].[Na+].Cl.[NH2:21][OH:22]>CC(O)C.C(OCC)(=O)C>[OH:22][N:21]=[C:5]([NH2:6])[C:4]1[CH:7]=[CH:8][C:9]([CH:11]=[CH2:12])=[CH:10][C:3]=1[C:2]([F:14])([F:13])[F:1]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 66955245HCID 66955245, compound

Product 1

HCID 86656395HCID 86656395, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 2-(trifluoromethyl)-4-vinylbenzonitrile (450 mg, 2.282 mmol) and sodium bicarbonate (767 mg, 9.13 mmol) in 2-propanol (10 mL) was added hydroxylamine hydrochloride (317 mg, 4.56 mmol). The reaction mixture was heated at 85° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried with MgSO4, filtered, and concentrated to give 460 mg of N′-hydroxy-2-(trifluoromethyl)-4-vinylbenzimidamide. MS (m+1)=231. HPLC Peak RT=0.78 minutes (Analytical Method B).

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9cea15aa31694805989c2ced43a34b01
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

Loading…