Formaldehyde → HCID 178463123, compound

HRID 1738358Notes

Reaction equation

HRID 1738358 reaction equation
[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:26])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:12]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[C:11]=2[Cl:25])[CH:5]=[N:4]1)[CH3:2].[CH2:27]=O>ClCCl.C(OCC)C>[CH2:1]([N:3]1[C:7]([OH:8])=[C:6]([C:9](=[O:26])[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[C:12]([N:20]3[CH2:21][CH2:22][CH2:23][O:24][CH2:27]3)[C:11]=2[Cl:25])[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 712FormaldehydeHCID 178463130HCID 178463130, compound

Product 1

HCID 178463123HCID 178463123, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 350 mg (0.87 mmol) of 1-ethyl-4-(2-chloro-3-(3-hydroxypropylamino)-4-methylsulfonylbenzoyl)-5-hydroxypyrazole in 1 mL of dichloromethane was diluted with 10 mL of diethyl ether and treated with 0.10 mL (1.3 mmol) of formalin. After stirring for 40 hours at ambient temperature, the reaction mixture contained a white precipitate and approximately one third of the starting material remained according to HPLC analysis. The solution was decanted and the solids remaining were dissolved in dichloromethane. The resulting solution was washed with water, dried over sodium sulfate, and concentrated by evaporation under reduced pressure. The residue was recrystallized from ethyl acetate to obtain 160 mg (43 percent of theory) of the title compound as tan crystals.

Workup

  1. customThe solution was decanted
  2. dissolutionthe solids remaining were dissolved in dichloromethane
  3. washThe resulting solution was washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-17aa8a9f7b114937ab07254381d1c0a8
Source dataset
uspto-grants-1999_10
Patent number
US05962690

Reaction notes

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