5-methoxy-3-(4-amino-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-one → 5-Methoxy-3-(4-(4-chlorobenzylamino)-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-one

HRID 840730Notes

Reaction equation

HRID 840730 reaction equation
[CH3:1][O:2][C:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([CH3:16])[CH:10]=2)[N:4]=1.[Cl:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[O:7][C:6](=[O:8])[N:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH2:22][C:21]3[CH:24]=[CH:25][C:18]([Cl:17])=[CH:19][CH:20]=3)=[C:11]([CH3:16])[CH:10]=2)[N:4]=1

Participants

4

Reactant 2

HCID 98778575-methoxy-3-(4-amino-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-oneHCID 131723164HCID 131723164, compound

Product 1

HCID 226202505-Methoxy-3-(4-(4-chlorobenzylamino)-3-methylphenyl)-3H-(1,3,4)-oxadiazol-2-one

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The latter compound was obtained by reacting 5-methoxy-3-(4-amino-3-methylphenyl)-3H-(1,3,4)oxadiazol-2-one with 4-chlorobenzaldehyde/sodium borohydride in methanol/methylene chloride at room temperature and was purified by column chromatography (silica gel, ethyl acetate:n-heptane=1:1).

Workup

  1. customThe latter compound was obtained
  2. customat room temperature
  3. customwas purified by column chromatography (silica gel, ethyl acetate:n-heptane=1:1)

Sources & evidence

ORD record
ord-06d92ae3f2934f63b0ef1a69ec234efb
Source dataset
uspto-grants-2002_04
Patent number
US06369088B2

Reaction notes

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