Sodium Dithionite → HCID 58747008, compound

HRID 915840Notes

Reaction equation

HRID 915840 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH2:9]([O:11][C:12]([C:14]1[C:18]([N:19]=O)=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)[N:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[N:15]=1)=[O:13])[CH3:10].C(OCC)(=O)C.CCCCCC>C(OCC)(=O)C.O>[CH2:9]([O:11][C:12]([C:14]1[C:18]([NH2:19])=[C:17]([C:21]2[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=2)[N:16]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[Cl:34])[N:15]=1)=[O:13])[CH3:10]

Participants

6

Reactant 3

HCID 24489Sodium DithioniteHCID 21226206Ethyl acetate hexaneHCID 86594819HCID 86594819, compound

Product 1

HCID 58747008HCID 58747008, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2-Chlorophenyl)-5-(4-chlorophenyl)4-nitroso-1H-pyrazole-3-carboxylic acid ethyl ester obtained from the last step was dissolved in ethyl acetate (200 ml) and water (200 ml). Sodium dithionite was added until the disappearance of 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-nitroso-1H-pyrazole-3-carboxylic acid ethyl ester was confirmed by TLC (ethyl acetate/hexane, 50/50). The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate and the solvent was removed, in vacuo. The red solid obtained was further purified by plug filtration (silica, ethyl acetate/hexane, 50/50) to give 4-amino-1-(2-chlorophenyl)-5-(4-chlorophenyl)-1H-pyrazole-3-carboxylic acid ethyl ester I-2A-1a (21.86 g, 76%). MS: 376.1 (M+1)+.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. customthe solvent was removed, in vacuo
  5. customThe red solid obtained
  6. filtrationwas further purified by plug filtration (silica, ethyl acetate/hexane, 50/50)

Sources & evidence

ORD record
ord-6914de4dd1494d16b6f32941837bed00
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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