Sodium Dithionite → HCID 12069414, compound

HRID 413782Notes

Reaction equation

HRID 413782 reaction equation
[C:1]([O:5][C:6](=[O:19])[N:7]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-])=O)[CH3:8])([CH3:4])([CH3:3])[CH3:2].O1CCOCC1.S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>O>[C:1]([O:5][C:6](=[O:19])[N:7]([C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[NH2:16])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24489Sodium DithioniteHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 15544598tert-butyl N-(5-chloro-2-nitrophenyl)-N-methylcarbamate

Product 1

HCID 12069414HCID 12069414, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (6.0 g), dioxane (150 ml), water (30 ml), sodium hydrosulfite (14.6 g) and sodium hydrogencarbonate (17.6 g) was heated under reflux for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate/n-hexane (1/3) as the eluant to afford the title compound (2.98 g). Rf=0.23 (thin-layer chromatography on a silica gel plate using ethyl acetate/n-hexane (1/3) as the eluant).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customThe reaction mixture was partitioned between ethyl acetate and water
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a silica gel column

Sources & evidence

ORD record
ord-39d4eda23219442bac3081b0e0a9de19
Source dataset
uspto-grants-2003_05
Patent number
US06569877B2

Reaction notes

Loading…