Benzaldehyde → HCID 86702438, compound

HRID 2203267Notes

Reaction equation

HRID 2203267 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([CH:16]([CH2:19][NH2:20])[CH2:17][NH2:18])=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+].II.[O-]S([O-])=O.[Na+].[Na+]>CC(O)(C)C>[Cl:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]2[CH2:19][NH:20][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:18][CH2:17]2)=[CH:14][CH:15]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 807IodineHCID 11430Potassium CarbonateHCID 24437Sodium SulfiteHCID 14010516HCID 14010516, compound

Product 1

HCID 86702438HCID 86702438, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of benzaldehyde (0.0056 mL, 0.056 mmol) and 2-(4-chlorophenyl)propane-1,3-diamine (10.8 mg, 0.059 mmol) in 0.7 mL t-BuOH was heated at 70° C. for 15 min. The reaction mixture was cooled to rt and treated with K2CO3 (38.5 mg, 0.279 mmol) and iodine (17.7 mg, 0.070 mmol). The reaction mixture was stirred for 5 min at rt and then heated to 70° C. for 2.5 hours. The reaction mixture was cooled to rt and saturated aqueous Na2SO3 was added drop-wise until the color changed from orange to yellow. The reaction mixture was partitioned between EtOAc and aqueous Na2CO3 solution, the EtOAc layer washed with H2O, brine, dried with anhydrous Na2SO4 and concentrated. The residue was chromatographed using basic aluminum oxide column and eluting with 5% MeOH/CHCl3 to give the title compound as an off-white solid (13.1 mg, 87%). 1H NMR (CDCl3) δ: 7.67-7.70 (m, 2H), 7.36-7.43 (m, 3H), 7.30-7.32 (m, 2H), 7.14-7.18 (m, 2H), 3.70 (dd, J=12.9, 4.4 Hz, 2H), 3.50 (dd, J=13.5, 10.3 Hz, 2H), 3.00 (tt, J=10.0, 4.8 Hz, 1H).

Workup

  1. temperatureheated to 70° C. for 2.5 hours
  2. temperatureThe reaction mixture was cooled to rt
  3. customThe reaction mixture was partitioned between EtOAc and aqueous Na2CO3 solution
  4. washthe EtOAc layer washed with H2O, brine
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated
  7. customThe residue was chromatographed
  8. washeluting with 5% MeOH/CHCl3

Sources & evidence

ORD record
ord-e6bab6d6517047299b3294072f0ed5a9
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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