Sodium Dithionite → 2-Hydroxyiminostilbene

HRID 718084Notes

Reaction equation

HRID 718084 reaction equation
[CH:1]1[C:2](=[O:16])[CH:3]=[CH:4][C:5]2=[N:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]=12.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)(Cl)Cl.O>[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][C:2]=1[OH:16]

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 2764572h-dibenzo[b,f]azepin-2-one

Product 1

HCID 131038642-HydroxyiminostilbeneYield 65%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Title compound 374 (170 mg, 0.82 mmol) was solubilized in CHCl3 (5 mL) and a saturated solution of Na2S2O4 in water was added (20 mL). The mixture was stirred for 3 hours. The 2 layers were split and the organic layer was dried over sodium sulfate, filtered and evaporated to afford title compound 375 (110 mg, 65%). MS (m/z): 209.9 (M+H).

Workup

  1. customThe 2 layers were split
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4f0b5f48cf83455180d7dd053a210197
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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