4-Ethoxybenzaldehyde → HCID 22036188, compound

HRID 1789664Notes

Reaction equation

HRID 1789664 reaction equation
[CH3:1][S:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH:17]=O)=[CH:15][CH:14]=1)[CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH2:10]([O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH:7][C:6]2[CH:8]=[CH:9][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:14]=1)[CH3:11]

Participants

5

Reactant 3

HCID 248344-EthoxybenzaldehydeHCID 660384-(Methylthio)anilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22036188HCID 22036188, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5.0 mL (40.19 mmol) of 4-(methylthio)aniline dissloved in 25 mL dichloromethane was added 5.59 mL (40.19 mmol) 4-ethoxybenzaldehyde followed by 12.78 g (60.28 mmol) sodium triacetoxyborohydride. The mixture was stirred at overnight at room temperature, partitioned between EtOAc and brine, dried over MgSO4 and concentrated. Crystallization from dichloromethane/hexane, provided 7.87 g of (4-Ethoxy-benzyl)-(4-methylsulfanylphenyl)-amine, pure by 1H NMR.

Workup

  1. custompartitioned between EtOAc and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customCrystallization from dichloromethane/hexane

Sources & evidence

ORD record
ord-b05e5be89b384b4d9231d6e40f8e8eac
Source dataset
uspto-grants-2006_07
Patent number
US07071177B2

Reaction notes

Loading…