Benzaldehyde → Methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetate

HRID 857158Notes

Reaction equation

HRID 857158 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[C:7]([Cl:20])[CH:6]=1.[CH:22](=O)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)=[C:7]([Cl:20])[CH:6]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21867227HCID 21867227, compound

Product 1

HCID 21867255Methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetateYield 88.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture consisting of methyl[3,5-dichloro-4-(4-aminophenoxy)phenyl]acetate (0.32 g), benzaldehyde (0.20 g), sodium cyanoborohydride (0.03 g), methanol (15 mL) and one drop of acetic acid was stirred at room temperature for 5 days. The reaction mixture was concentrated and the residue partionated between ethyl acetate and sodium hydrogen-carbonate (saturated aqueous solution). The aqueous phase was further extracted with ethyl acetate. The collected organic phases were purified on column (silica gel, n-heptane/ethyl acetate, 9:1) to give 0.36 g of methyl[3,5-dichloro-4-(4-benzylaminophenoxy)phenyl]acetate.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe aqueous phase was further extracted with ethyl acetate
  3. customThe collected organic phases were purified on column (silica gel, n-heptane/ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-20959f241126469db4f1c93a84be82a3
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

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