Sodium Bicarbonate → HCID 67041941, compound

HRID 1929288Notes

Reaction equation

HRID 1929288 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[NH:15][C:16](=O)[C:17]([CH3:20])([CH3:19])[CH3:18].CSC.B.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[C:3]=1[NH:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12423031(Dimethyl sulfide)trihydroboronHCID 67105486HCID 67105486, compound

Product 1

HCID 67041941HCID 67041941, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.76 g (10.47 mmol) of methyl 4-bromo-3-[(2,2-dimethylpropanoyl)amino]-2-nitro-benzoate were suspended in toluene and admixed with 6 ml (11.26 mmol) of borane-dimethyl sulfide (2M in toluene). The mixture was left with stirring under reflux for 15 h and then cooled. Thereafter, 50 ml of saturated NaHCO3 solution were added, stirring was carried out again at RT for 30 min, and then the organic phase was separated off, dried over MgSO4 and concentrated. The product was then subjected to chromatographic separation (silica gel, heptane/ethyl acetate 4:1).

Workup

  1. waitThe mixture was left
  2. temperatureunder reflux for 15 h
  3. temperaturecooled
  4. stirringstirring
  5. customthe organic phase was separated off
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe product was then subjected to chromatographic separation (silica gel, heptane/ethyl acetate 4:1)

Sources & evidence

ORD record
ord-87e3d048c2ac42a2be759f09e4212a41
Source dataset
uspto-grants-2012_05
Patent number
US08188002B2

Reaction notes

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