Hydrochloric Acid → HCID 68546459, compound

HRID 2359880Notes

Reaction equation

HRID 2359880 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:4]=1[CH2:5][NH:6][C:7](=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[B].CSC.Cl.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[C:4]=1[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 68550289HCID 68550289, compound

Product 1

HCID 68546459HCID 68546459, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7.5 g (23.71 mmol) N-(2,6-dimethoxybenzyl)-2-nitrobenzamide was dissolved in 130 mL THF, then 9.06 g boron-dimethyl sulfide-complex (2M solution in THF) was added by drops and the mixture was refluxed for 5 hours. Next 50 mL 2N HCl was added and the mixture was heated again at reflux for 30 minutes. For workup, the mixture was poured into water after cooling, a pH of approx. 10 was adjusted by adding 2N NaOH, further extraction was performed with ethyl acetate and the combined organic phases were dried with MgSO4. The crude product obtained by chromatography on silica gel (dichloromethane, 0-5% methanol) after filtration and evaporation yielded the desired amine; 3.58 g as a light yellow oil. ESI-MS [M+H+]=302.15.

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. temperaturethe mixture was heated again
  3. temperatureat reflux for 30 minutes
  4. temperatureafter cooling
  5. additionby adding
  6. extraction2N NaOH, further extraction
  7. dry with materialthe combined organic phases were dried with MgSO4
  8. customThe crude product obtained by chromatography on silica gel (dichloromethane, 0-5% methanol)
  9. filtrationafter filtration and evaporation

Sources & evidence

ORD record
ord-1e1dc069ed054d109c25d9f75966b42b
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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