Hydrochloric Acid → HCID 21930345, compound

HRID 1243673Notes

Reaction equation

HRID 1243673 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:19]([O-:21])=[O:20])=[C:7]([S:9][C:10]2[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=2)[C:13]([NH2:15])=O)[CH:8]=1.B.[ClH:23].[OH-].[K+]>C1COCC1>[ClH:23].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:19]([O-:21])=[O:20])=[C:7]([S:9][C:10]2[CH:11]=[C:12]([CH2:13][NH2:15])[CH:16]=[CH:17][CH:18]=2)[CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 14797Potassium HydroxideHCID 21930401HCID 21930401, compound

Product 1

HCID 21930345HCID 21930345, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3-[(5-Methoxy-2-nitrophenyl)thio]benzamide (0.6 g, 1.97 mmol) in THF (25 ml) was treated with 1M borane in THF (10 ml, 9.86 mmol) at 0° C. with stirring. The clear solution was heated under reflux with stirring for 24 h under nitrogen. The reaction mixture was cooled, treated with 5N hydrochloric acid (20 ml) and stirred for 1 h. The mixture was cooled to 0° C., basified with solid potassium hydroxide and extracted with ethyl acetate. The extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue eluted down a silica column using 5% methanol/dichloromethane as eluent to give a yellow solid (0.414 g, 72%).

Workup

  1. temperatureThe clear solution was heated
  2. temperatureunder reflux
  3. stirringwith stirring for 24 h under nitrogen
  4. temperatureThe reaction mixture was cooled
  5. stirringstirred for 1 h
  6. extractionextracted with ethyl acetate
  7. washThe extracts were washed with brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent was evaporated
  10. washthe residue eluted down a silica column

Sources & evidence

ORD record
ord-3ff454c692824a46b280a8e5d6642856
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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