(3-Amino-phenyl)-carbamic acid benzyl ester → HCID 59138727, compound

HRID 970662Notes

Reaction equation

HRID 970662 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:6][CH:7]=1>C(O)C>[CH:11]([C:12]1[CH:13]=[N:1][C:2]2[C:7]([CH:17]=1)=[CH:6][CH:5]=[C:4]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:3]=2)=[O:10]

Participants

3

Reactant 1

HCID 12941491(3-Amino-phenyl)-carbamic acid benzyl ester

Product 1

HCID 59138727HCID 59138727, compoundYield 197.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of benzyl 3-aminophenylcarbamate (8.0 g, 0.033 mol) and 2-dimethylaminomethylene-1,3-bis(dimethylimmonio)propane bis(tetrafluoroborate) (31 g, 0.087 mol) in ethanol (400 mL) was heated at reflux for 24 h. The solution was concentrated under vacuum and the residue was dissolved in THF (200 mL) and 1N HCl (200 mL). The reation mixture was stirred at rt overnight, then poured into a saturated solution of sodium bicarbonate (200 mL), and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated under vacuum to afford the desired product (10.0 g, 99%) as a yellow solid. LC-MS: 2.84 min, 307.1 (M+1).

Workup

  1. temperatureat reflux for 24 h
  2. concentrationThe solution was concentrated under vacuum
  3. dissolutionthe residue was dissolved in THF (200 mL)
  4. additionpoured into a saturated solution of sodium bicarbonate (200 mL)
  5. extractionextracted with EtOAc (2×)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9ce9ef2000d04ad293728e0a9a058d8c
Source dataset
uspto-grants-2007_12
Patent number
US07312233B2

Reaction notes

Loading…