Formaldehyde → HCID 178482827, compound

HRID 2351017Notes

Reaction equation

HRID 2351017 reaction equation
Cl.[CH3:2][NH2:3].O1CCCC1.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][S:15][CH2:16][CH2:17][NH:18][C:19]([NH:25][CH2:26][CH:27]([OH:35])[C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1)=[N:20][S:21]([CH3:24])(=[O:23])=[O:22].[OH-].[Na+].[CH2:38]=O>O>[OH:35][CH:27]([C:28]1[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=1)[CH2:26][NH:25][C:19]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])=[N:18][CH2:17][CH2:16][S:15][CH2:14][C:10]1[O:9][C:13]([CH2:2][NH:3][CH3:38])=[CH:12][CH:11]=1

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 6364545Methylamine hydrochlorideHCID 178505160HCID 178505160, compound

Product 1

HCID 178482827HCID 178482827, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

240 mg of methylamine hydrochloride was dissolved in a 0.27 ml of 37% (w/w) aqueous formalin solution. Thereto was added, at room temperature, 2.5 ml of a tetrahydrofuran solution containing 500 mg of N-[2-[(2-furyl)methylthio]ethyl]-N'-[2-hydroxy-2(4-hydroxyphenyl)ethyl]-N"-methanesulfonylguanidine. The mixture was stirred at the same temperature for 5 hours. The reaction mixture was introduced into 30 ml of water. The resulting mixture was adjusted to pH 9.5 with a 1N aqueous sodium hydroxide solution and extracted with two 50-ml portions of a 1:1 mixture of ethyl acetate and tetrahydrofuran. The extracts were combined and dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography (eluant:chloroform:methanol:aqueous ammonia solution=85:15:1) to obtain 220 mg (yield: 40%) of N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-N'-methanesulfonyl-N"-[2-[[5-(methylamino)methyl-2-furyl]methylthio]ethyl]guanidine.

Workup

  1. additionThereto was added, at room temperature
  2. extractionextracted with two 50-ml portions of a 1:1 mixture of ethyl acetate and tetrahydrofuran
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by a column chromatography (eluant:chloroform:methanol:aqueous ammonia solution=85:15:1)

Sources & evidence

ORD record
ord-8c6dc5052d5340eeb7cf12bcbd35b276
Source dataset
uspto-grants-1989_10
Patent number
US04871765

Reaction notes

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