Hydrochloric Acid → HCID 178426111, compound

HRID 1732384

Reaction equation

HRID 1732384 reaction equation
C[O-:2].[Na+].[Na].NO.Cl.C[N:9](C)[CH:10]=[N:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH3:19]>CO.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][CH:10]=[N:9][OH:2])=[C:13]([CH3:19])[CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 22544ChlordimeformHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 178426111HCID 178426111, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a sodium methoxide solution prepared by dissolving 19 grams of sodium metal in 250 milliliters of methanol was added 56 grams of hydroxylamine:hydrochloride in 300 milliliters of methanol. To the resulting mixture was added 98 grams (0.5 mole) of N,N-dimethyl-N'-(4-chloro-2-methylphenyl)methanimidamide. The mixture was stirred at room temperature for 18 hours. The solid reaction product was recovered by filtration and the filtrate concentrated by evaporation under reduced pressure. The residue and the solid reaction product (filter cake) were suspended in water, collected by filtration, water washed and recrystallized from ethanol. The N-(4-chloro-2-methylphenyl)-N'-hydroxymethanimidamide product was recovered in a yield of 81.7 grams (89% of theoretical) and melted at 171°-171.5° C.

Workup

  1. customThe solid reaction product
  2. filtrationwas recovered by filtration
  3. concentrationthe filtrate concentrated by evaporation under reduced pressure
  4. customThe residue and the solid reaction product (filter cake)
  5. filtrationcollected by filtration, water
  6. washwashed
  7. customrecrystallized from ethanol
  8. customThe N-(4-chloro-2-methylphenyl)-N'-hydroxymethanimidamide product was recovered in a yield of 81.7 grams (89% of theoretical) and melted at 171°-171.5° C.

Sources & evidence

ORD record
ord-dbd04e5c2d42444180cea3c79f92479a
Source dataset
uspto-grants-1980_12
Patent number
US04237168

Linked notes

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