Formaldehyde → HCID 178455183, compound

HRID 1857731Notes

Reaction equation

HRID 1857731 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:13][N:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:23]=[O:24]>>[Si:1]([O:8][CH2:9][C:10]1[NH:11][C:12]([S:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[C:13]([CH2:23][OH:24])[N:14]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 22130557HCID 22130557, compound

Product 1

HCID 178455183HCID 178455183, compoundYield 33%

Procedure

An aqueous solution of 2.0 g (5.6 mmol) of 2-t-butyldimethylsilyloxymethyl-5-(3-chlorophenylthio)-1H-imidazole (45') in 37% formaline (10 ml) was heated at 120° C. for 10 hours in a sealed tube. The reaction mixture was washed out with methanol from the tube, dried over sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1), the crude product was washed with n-hexane, and filtered to give 716 mg of [2-t-butyldimethylsilyloxymethyl-5-(3-chlorophenylthio)-1H-imidazol-4-yl]methanol (46) (yield 33%). mp 136-137° C.

Workup

  1. washThe reaction mixture was washed out with methanol from the tube
  2. dry with materialdried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (ethyl acetate:n-hexane=1:1)
  5. washthe crude product was washed with n-hexane
  6. filtrationfiltered

Sources & evidence

ORD record
ord-d29602a35ca24979a2528518d63e64e1
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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