Hydrochloric Acid → HCID 974966, compound

HRID 703123Notes

Reaction equation

HRID 703123 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([NH:6][NH:7][C:8]([NH:10][CH3:11])=[S:9])=O.Cl.N1C=CC=CC=1.C([O-])(O)=O.[Na+].Cl>>[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]1[N:10]([CH3:11])[C:8](=[S:9])[NH:7][N:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 3438030HCID 3438030, compoundHCID 10176127Pyridinium chloride

Product 1

HCID 974966HCID 974966, compoundYield 48.1%

Procedure

1-(2-Fluorobenzoyl)-4-methylthiosemicarbazide (11.3 g, 4.97×10-2 mole) or the aforementioned mixture of the above and pyridine hydrochloride and 1 molar aqueous NaHCO3 (480 ml, 4.80×10-1 mole) were stirred and heated to reflux After refluxing overnight, the reaction was cooled in an ice bath before being acidified by the drop-wise addition of concentrated hydrochloric acid (40 ml, 4.8×10-1 mole). The resulting precipitate was collected by filtration, washed with a little H2O, and dried by suction. This afforded a colorless powder 5.0 g (48%). This material was of sufficient purity to go on to the next step. If desired this material could be crystallized from EtOAc/hexane affording colorless needles, mp 137°-139° C.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. temperatureAfter refluxing overnight
  4. temperaturethe reaction was cooled in an ice bath
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with a little H2O
  7. customdried by suction

Sources & evidence

ORD record
ord-1f08e5ec777e4c1484ebea629ce2b430
Source dataset
uspto-grants-1991_01
Patent number
US04981863

Reaction notes

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