Hydroxyamine hydrochloride → tert-Butyl [3-(N-Hydroxycarbamimidoyl)phenyl]carbamate

HRID 235244Notes

Reaction equation

HRID 235244 reaction equation
Cl.[NH2:2][OH:3].[O-]CC.[Na+].[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:11]=1)#[N:9]>C(O)C>[C:20]([O:19][C:17]([NH:16][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[C:8](=[N:2][OH:3])[NH2:9])=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 12129277tert-Butyl (3-cyanophenyl)carbamate

Product 1

HCID 53965079tert-Butyl [3-(N-Hydroxycarbamimidoyl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydroxylamine hydrochloride (3.16 g, 0.045 mol) was added to a stirred solution of sodium ethoxide in ethanol [prepared by dissolving 1.17 g of sodium in 70 ml of ethanol]. The mixture was stirred at room temperature for 15 min then 1-cyano-3-tert-butyloxycarbonylaminobenzene (3.00 g, 0.014 mol) was added. The mixture was heated at 50° C. overnight then cooled to ambient temperature. The mixture was then filtered and the filtrate evaporated in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (50 ml). The organic phase was separated and the aqueous phase extracted with ethyl acetate (3×20 ml). The organic layers were combined, washed with brine (50 ml) then dried (Na2SO4). The solvent was evaporated to leave a pink fo.m. The foam was left at 0° C. overnight, then triturated with 1:1 petrol:ethyl acetate. The title compound was collected as a white solid (2.52 g, 73%). 1H NMR (360 MHz, D6 -DMSO)δ1.47 (9H, s), 5.69 (2H, brs), 7.24 (2H, m), 7.41 (1H, brd, J=6.5 Hz), 7.82 (1H, s), 9.35 (1H, s), 9.58 (1H, s). MS (CI, NH3) 252 (M+1).

Workup

  1. temperatureThe mixture was heated at 50° C. overnight
  2. temperaturethen cooled to ambient temperature
  3. filtrationThe mixture was then filtered
  4. customthe filtrate evaporated in vacuo
  5. customThe residue was partitioned between ethyl acetate (50 ml) and water (50 ml)
  6. customThe organic phase was separated
  7. extractionthe aqueous phase extracted with ethyl acetate (3×20 ml)
  8. washwashed with brine (50 ml)
  9. dry with materialthen dried (Na2SO4)
  10. customThe solvent was evaporated
  11. customto leave a pink fo.m
  12. waitThe foam was left at 0° C. overnight
  13. customtriturated with 1:1 petrol
  14. customThe title compound was collected as a white solid (2.52 g, 73%)

Sources & evidence

ORD record
ord-27eddc161539464f9463c66182d92e8d
Source dataset
uspto-grants-1997_01
Patent number
US05597915

Reaction notes

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