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Ethyl Acetate → HCID 66966480, compound

HRID 1513264
Notes
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Reaction equation

HRID 1513264 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]3[CH:15]=[C:16]([NH2:21])[C:17]([NH2:20])=[CH:18][CH:19]=3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.[CH3:22][O:23][C:24](=[O:37])[CH:25]=[CH:26][C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([CH:34]=O)=[C:29]([CH3:36])[CH:28]=1.OOS([O-])=O.[K+].C(OCC)(=O)C>CN(C=O)C.O>[CH3:22][O:23][C:24](=[O:37])/[CH:25]=[CH:26]/[C:27]1[CH:32]=[C:31]([CH3:33])[C:30]([C:34]2[NH:21][C:16]3[CH:15]=[C:14]([C:12]4[O:13][C:9]([C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=5)=[N:10][N:11]=4)[CH:19]=[CH:18][C:17]=3[N:20]=2)=[C:29]([CH3:36])[CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 23707502Potassium hydroxy sulfiteHCID 669663924-[5-(4-Methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamineHCID 866328203-(4-Formyl-3,5-dimethylphenyl)-acrylic acid methyl ester

Product 1

HCID 66966480HCID 66966480, compound

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
2×
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl]-benzene-1,2-diamine (564 mg, 2.0 mmol) and 3-(4-formyl-3,5-dimethylphenyl)-acrylic acid methyl ester (436 mg, 2.0 mmol) (Example 1-60, step C) in 10 mL of DMF and 1 mL of water was added oxone (824 mg, 1.34 mmol) and the mixture was stirred at RT for 20 min. Ethyl acetate was added and stirred for a while then water was added. The organic layer was separated and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure to give the title compound. MS: m/z 481 (M+1).

Workup

  1. stirringstirred for a while
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5366e3c959da49dcaa9ea4282c3494a3
Source dataset
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08217065B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes