Borane;tetrahydrofuran → HCID 18005757, compound

HRID 1373119Notes

Reaction equation

HRID 1373119 reaction equation
[NH2:1][C:2]([CH2:4][N:5]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)[S:6]([CH3:9])(=[O:8])=[O:7])=O.B.C1COCC1>Cl>[NH2:1][CH2:2][CH2:4][N:5]([C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)[S:6]([CH3:9])(=[O:8])=[O:7]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 180057924-(N-aminocarbonylmethyl-N-methylsulphonyl-amino)-nitrobenzene

Product 1

HCID 18005757HCID 18005757, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2.3 g (8.4 mmol) of 4-(N-aminocarbonylmethyl-N-methylsulphonyl-amino)-nitrobenzene are refluxed in 35 ml (35 mmol) of borane-THF (1 M solution in THF) 7 hours. Then 30 ml of 6 N hydrochloric acid are added, and the mixture is refluxed for another 8 hours. The solvent is distilled off, the residue is mixed with water and extracted with ethyl acetate. The aqueous phase is made alkaline with potassium carbonate and extracted with dichloromethane. The organic phase is separated off, dried and evaporated down.

Workup

  1. temperaturethe mixture is refluxed for another 8 hours
  2. distillationThe solvent is distilled off
  3. additionthe residue is mixed with water
  4. extractionextracted with ethyl acetate
  5. extractionextracted with dichloromethane
  6. customThe organic phase is separated off
  7. customdried
  8. customevaporated down

Sources & evidence

ORD record
ord-7f2c346ceb704698aa3fe1fb27b6719f
Source dataset
uspto-grants-2007_01
Patent number
US07160901B2

Reaction notes

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