Sodium Bicarbonate → HCID 67266787, compound

HRID 602504Notes

Reaction equation

HRID 602504 reaction equation
[CH2:1]([O:4][C:5](=[O:17])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[CH:9][C:8]=1[Br:16])[CH2:2][CH3:3].C(=O)(O)[O-].[Na+]>C(O)C.Cl.[Fe]>[CH2:1]([O:4][C:5](=[O:17])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[Br:16])[CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 67267172HCID 67267172, compound

Product 1

HCID 67266787HCID 67266787, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

A suspension of iron powder (20 g, excess) and (2-Bromo-4-nitrophenyl)-carbamic acid propyl ester (2.183 g, 7.20 mmol) in ethanol (80 mL) and 6 M aqueous hydrochloric acid (20 mL) was sonicated at room temperature for 10 minutes. The mixture was slowly poured into saturated aqueous sodium bicarbonate (NaHCO3) solution, filtered and extracted with ethyl acetate. The combined organic solution was washed 3 times with saturated aqueous NaHCO3, dried over sodium sulfate (Na2SO4) and evaporated in vacuo to give 1.67 g of the title compound as pale yellow oil which solidified. Yield 85%. LC/MS (m/z) 271.9, 273.8 (M+); RT=1.30, (UV, ELSD) 99%, 100%. 1H NMR (DMSO-d6): 0.90 (br. s (unresolved t), 3H), 1.59 (br. s (unresolved m), 2H), 3.94 (t, 2H), 5.31 (s, 2H, NH2), 6.50 (dd, 1H), 6.80 (unresolved d, 1H), 6.96 (br. d, 1H), 8.51 (br. s, NHCO).

Workup

  1. customwas sonicated at room temperature for 10 minutes
  2. filtrationfiltered
  3. extractionextracted with ethyl acetate
  4. washThe combined organic solution was washed 3 times with saturated aqueous NaHCO3
  5. dry with materialdried over sodium sulfate (Na2SO4)
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-95e9d3c7bab04cef992632a4649ca359
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

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