Hydroxylamine → HCID 178485198, compound

HRID 1974195Notes

Reaction equation

HRID 1974195 reaction equation
[NH2:1][OH:2].Cl.NO.[OH-].[K+].CS[C:10](=[N:20][CH3:21])[N:11]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH3:12]>CO>[CH2:13]([N:11]([CH3:12])[C:10]([NH:20][CH3:21])=[N:1][OH:2])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 21488972HCID 21488972, compound

Product 1

HCID 178485198HCID 178485198, compoundYield 1.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 100 ml. solution of hydroxylamine generated from hydroxylamine hydrochloride (5.86 g., 0.088 mol) and potassium hydroxide (4.59 g., 0.088 mol) was cooled to 0°. To this was added a 25 ml. methanol solution of S-methyl-N-benzyl-N,N'-dimethylisothiourea (3.53 g., 0.017 mol) over a 10 minute period. The mixture was allowed to stir for 4 hours. Methanol was then removed by evaporation and the residue redissolved in methylene chloride. After two washes with 100 ml. quantities of water, the organic layer was extracted with 20 ml. 1N hydrochloric acid. The aqueous layer was then made basic to pH 9 and extracted with methylene chloride. The organic layer was dried, evaporated, and resulted in 0.100 g. of an oil. The oil was separated into its components using high pressure liquid chromatography and 40 mg. (1.2% yield) of pure 1-benzyl-1,3-dimethyl-2-hydroxyguanidine was isolated. It had thin layer chromatographic and NMR properties identical to those of an authentic sample.

Workup

  1. temperaturewas cooled to 0°
  2. additionTo this was added a 25 ml
  3. customMethanol was then removed by evaporation
  4. dissolutionthe residue redissolved in methylene chloride
  5. extractionquantities of water, the organic layer was extracted with 20 ml
  6. extractionextracted with methylene chloride
  7. customThe organic layer was dried
  8. customevaporated
  9. customresulted in 0.100 g
  10. customThe oil was separated into its components

Sources & evidence

ORD record
ord-6301670a496a475bbf52d1af1cb63e9e
Source dataset
uspto-grants-1976_12
Patent number
US04000196

Reaction notes

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