Sodium Dithionite → HCID 15679994, compound

HRID 1494174Notes

Reaction equation

HRID 1494174 reaction equation
[I-].[CH:2]1[C:12]2[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=3[N:7]([CH2:17][CH2:18][CH2:19][N:20]([C:22]([O:24][CH2:25][O:26][C:27]([C:29]3[CH:30]=[N+:31]([CH3:35])[CH:32]=[CH:33][CH:34]=3)=[O:28])=[O:23])[CH3:21])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.C(OCC)(=O)C>[CH3:35][N:31]1[CH:32]=[CH:33][CH2:34][C:29]([C:27]([O:26][CH2:25][O:24][C:22]([N:20]([CH2:19][CH2:18][CH2:17][N:7]2[C:6]3[CH:5]=[CH:4][CH:3]=[CH:2][C:12]=3[CH2:11][CH2:10][C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]2=3)[CH3:21])=[O:23])=[O:28])=[CH:30]1

Participants

6

Reactant 3

HCID 24489Sodium DithioniteHCID 516892Sodium BicarbonateHCID 15679990HCID 15679990, compound

Product 1

HCID 15679994HCID 15679994, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Three-tenths gram (0.0005 mol) of the product of Example 54 in 30 mL water and 15 mL ethyl acetate was reduced with 0.25 g (0.003 mol) NaHCO3 and 0.35 g (0.002 mol) sodium dithionite at 0°-5° C., with deaeration, for a 60 minute period. The layers were separated and the aqueous layer was extracted twice with 30 mL portions of ethyl acetate. The combined organic layers were then extracted twice with 20 mL portions of cool deaerated water. Drying over Na2SO4 and removal of the solvent in vacuo afforded 0.22 g (95%) of the title compound, melting at 59°-63° C. (dec.) and having the structural formula: ##STR96##

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with 30 mL portions of ethyl acetate
  3. extractionThe combined organic layers were then extracted twice with 20 mL portions of cool deaerated water
  4. dry with materialDrying over Na2SO4 and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-ee8232495f0a474fa87b1eb042d88304
Source dataset
uspto-grants-1991_06
Patent number
US05024998

Reaction notes

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