Sodium Dithionite → HCID 58747008, compound

HRID 859190Notes

Reaction equation

HRID 859190 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

The product obtained from the last step was dissolved in 200 ml of ethyl acetate and 200 ml of water. 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). Then 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-4a (21.86 g, 76%). MS: 376.1 (M+1)+.

Workup

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

Sources & evidence

ORD record
ord-1caa87e16c014515b16b4c2680f8db73
Source dataset
uspto-grants-2006_12
Patent number
US07151097B2

Reaction notes

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