Hydrochloric Acid → HCID 974966, compound

HRID 257159Notes

Reaction equation

HRID 257159 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, compound

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 dropwise 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. 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 to reflux
  2. temperatureAfter refluxing overnight
  3. temperaturethe reaction was cooled in an ice bath
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with a little H2O
  6. customdried by suction
  7. customThis afforded a colorless powder
  8. customcould be crystallized from EtOAc/hexane affording colorless needles, Mp 137°-139° C.

Sources & evidence

ORD record
ord-0dc35b6642354aa29a0735bb4a57e0f8
Source dataset
uspto-grants-1993_11
Patent number
US05260450

Reaction notes

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