Hydrochloric Acid → HCID 86723942, compound

HRID 1475313Notes

Reaction equation

HRID 1475313 reaction equation
[C:1]1([S:7]([C:10]2[CH:11]=[C:12]([NH:16]N)[CH:13]=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:18](=O)[CH:19]([CH3:21])[CH3:20].Cl.O1CCOCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C.C1(C)C=CC=CC=1>[C:1]1([S:7]([C:10]2[CH:11]=[C:12]3[C:13]([C:19]([CH3:21])([CH3:20])[CH2:18][NH:16]3)=[CH:14][CH:15]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6561IsobutyraldehydeHCID 312751,4-DioxaneHCID 5049666Sodium triacetoxyborohydrideHCID 70981569HCID 70981569, compound

Product 1

HCID 86723942HCID 86723942, compoundYield 4.6%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of (3-benzenesulfonyl-phenyl)-hydrazine (0.824 g, 3.3 mmol), isobutyraldehyde (0.245 g, 3.4 mmol) and toluene (12 mL) was stirred at 20° C. for 2 h. Acetic acid (12 mL) was added, followed by a solution of HCl in 1,4-dioxane (4 M, 0.83 mL, 3.3 mmol) and stirring was continued for 2 h. 1,2-Dichloroethane (12 mL) was added followed by sodium triacetoxyborohydride (1.05 g, 5 mmol) and stirring was continued for 1 h. The mixture was concentrated to 5 mL in vacuo and residue partitioned between saturated aqueous sodium hydrogen carbonate (200 mL) and DCM (3×60 mL). The combined organic extracts were dried (Na2SO4) and evaporated in vacuo to give an orange oil. Chromatography (SiO2; gradient elution with 0-30% Et2O in petrol) gave the title compound (0.044 g). MS: [M+H]+=288.

Workup

  1. stirringstirring
  2. waitwas continued for 2 h
  3. stirringstirring
  4. waitwas continued for 1 h
  5. concentrationThe mixture was concentrated to 5 mL in vacuo and residue
  6. custompartitioned between saturated aqueous sodium hydrogen carbonate (200 mL) and DCM (3×60 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. customevaporated in vacuo
  9. customto give an orange oil
  10. washChromatography (SiO2; gradient elution with 0-30% Et2O in petrol)

Sources & evidence

ORD record
ord-e5022cc1cc544514be8f4b44834e2055
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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