Sodium Dithionite → HCID 10903842, compound

HRID 1266146Notes

Reaction equation

HRID 1266146 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH:7]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=1)=[O:14])[CH2:8]2)([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>CN(C)C=O.O>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH:7]([C:13]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:18][CH:17]=1)=[O:14])[CH2:8]2

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 18548990HCID 18548990, compound

Product 1

HCID 10903842HCID 10903842, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of the crude nitro compound (3.5 g) in N,N-dimethylformamide (25 mL) and water (3 mL) was added, in portions, sodium dithionite (7.0 g, 40 mmol). The mixture was stirred at 90° C. for 3 hours. The solvent was evaporated in vacuo and water (200 mL) was added. The mixture was made alkaline with 2 M sodium hydroxide and extracted with chloroform. The phases were separated and the organic phase was dried (Na2SO4), filtered and evaporated in vacuo to give 1.1 g of the crude product (GC purity 89%): EIMS (70 eV) m/z (relative intensity) 337 (100, M+).

Workup

  1. customThe solvent was evaporated in vacuo and water (200 mL)
  2. additionwas added
  3. extractionextracted with chloroform
  4. customThe phases were separated
  5. dry with materialthe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6fff36af9c01402da445dc977da22caf
Source dataset
uspto-grants-2003_04
Patent number
US06548498B1

Reaction notes

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