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Sodium Thiosulfate → HCID 58542019, compound

HRID 1966678
Notes
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Reaction equation

HRID 1966678 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:13])[C:5]([NH:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:6][CH:7]=1.[CH3:14][C:15]1[N:19]=[C:18]([C:20]2[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=2[CH:22]=O)[O:17][N:16]=1.OOS([O-])=O.[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([C:9]([CH3:10])([CH3:12])[CH3:11])[C:22]([C:21]3[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=3[C:18]3[O:17][N:16]=[C:15]([CH3:14])[N:19]=3)=[N:13][C:4]=2[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 23707502Potassium hydroxy sulfiteHCID 242295022-(3-Methyl-1,2,4-oxadiazol-5-yl)benzaldehydeHCID 431486354-bromo-N1-tert-butylbenzene-1,2-diamine

Product 1

HCID 58542019HCID 58542019, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-N1-tert-butyl-benzene-1,2-diamine (700 mg, 2.8 mmol) in DMF (15 mL) is added 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzaldehyde (813 mg, 4.3 mmol) at room temperature. Oxone (1.7 g, 2.8 mmol) in H2O (4 mL) is added and the solution is stirred for 1 hour. Saturated sodium thiosulfate solution (10 mL) is added and the mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL). The combined organic layer is dried, (MgSO4), filtered and concentrated. The residue is purified by silica gel flash column chromatography eluting with 10% MeOH in CH2Cl2 to afford the 5-bromo-1-tert-butyl-2-[2-(3-methyl-1,2,4-oxadiazol-5-yl)-phenyl]-1H-benzimidazole (900 mg, 76%) as a pale brown solid.

Workup

  1. extractionthe mixture is extracted with EtOAc (3×10 mL) and H2O (10 mL)
  2. dry with materialThe combined organic layer is dried, (MgSO4),
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue is purified by silica gel flash column chromatography
  6. washeluting with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-2d695dc246804cf2aa3fd97561fb9778
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08420655B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes