Sodium Bicarbonate → HCID 178491174, compound

HRID 1967462Notes

Reaction equation

HRID 1967462 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[CH3:8][O:9][C:10]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:11]=1[CH2:12][NH:13][C:14]([C:16]1[C:20]([N+:21]([O-])=O)=[CH:19][NH:18][N:17]=1)=[O:15].C(Cl)Cl.CO.C(=O)([O-])O.[Na+]>C(O)C>[CH3:8][O:9][C:10]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:11]=1[CH2:12][NH:13][C:14]([C:16]1[C:20]([NH2:21])=[CH:19][NH:18][N:17]=1)=[O:15]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 21226129Dichloromethane methanolHCID 85782573Tin tetrachloride dihydrateHCID 178491175HCID 178491175, compound

Product 1

HCID 178491174HCID 178491174, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

27.64 g of tin chloride dihydrate are added portionwise to a suspension of 10.72 g of 4-nitro-1H-pyrazole-3-carboxylic acid 2,4-dimethoxybenzylamide in 600 ml of absolute ethanol. The reaction medium is stirred for 48 hours at 20° C. The clear brown solution obtained is brought to dryness on a rotary evaporator. The clear brown foam obtained is taken up in 700 ml of a 90/10 by volume a mixture of methylene chloride/methanol. 700 ml of saturated aqueous sodium hydrogen carbonate solution are added to the brown solution obtained. The cream-colored suspension obtained is stirred for 1 hour at room temperature. 30 g of Clarcel Flo are added to the suspension and the mixture is then stirred for 10 minutes at room temperature. The resulting mixture is filtered and the filter cake is washed with twice 250 ml of a 90/10 by volume a mixture of methylene chloride/methanol. The solid is drained by suction and the filtrate is recovered and then transferred into a separating funnel. The chloromethylene phase is separated out by settling and the aqueous phase is then re-extracted with twice 250 ml of dichloromethane. The organic phases are combined and then dried over magnesium sulfate, filtered through paper and then brought to dryness on a rotary evaporator. 8.53 g of 4-amino-1H-pyrazole-3-carboxylic acid 2,4-dimethoxybenzylamide are obtained in the form of a pale pink solid. ([M+H]+): 277). RT: 2.36 min (Method A).

Workup

  1. customThe clear brown solution obtained
  2. customis brought to dryness on a rotary evaporator
  3. customThe clear brown foam obtained
  4. customobtained
  5. customThe cream-colored suspension obtained
  6. stirringis stirred for 1 hour at room temperature
  7. addition30 g of Clarcel Flo are added to the suspension
  8. stirringthe mixture is then stirred for 10 minutes at room temperature
  9. filtrationThe resulting mixture is filtered
  10. washthe filter cake is washed with twice 250 ml of a 90/10 by volume
  11. additiona mixture of methylene chloride/methanol
  12. customthe filtrate is recovered
  13. customtransferred into a separating funnel
  14. customThe chloromethylene phase is separated out
  15. extractionthe aqueous phase is then re-extracted with twice 250 ml of dichloromethane
  16. dry with materialdried over magnesium sulfate
  17. filtrationfiltered through paper
  18. custombrought to dryness on a rotary evaporator

Sources & evidence

ORD record
ord-cc71b5ec8920418089f1eaab329e6fd8
Source dataset
uspto-grants-2013_04
Patent number
US08420824B2

Reaction notes

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