Benzene → HCID 21413063, compound

HRID 2071231Notes

Reaction equation

HRID 2071231 reaction equation
C1([NH:7][NH:8][C:9]2[S:10][CH2:11][CH2:12][N:13]=2)C=CC=CC=1.N1C=CC=CC=1.[CH:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:26]1([CH2:32][C:33](Cl)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O>[C:26]1([CH2:32][C:33]([NH:7][N:8]([C:9]2[S:10][CH2:11][CH2:12][N:13]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 1049PyridineHCID 7679Phenylacetyl chlorideHCID 2306203HCID 2306203, compound

Product 1

HCID 21413063HCID 21413063, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.0 g. of 2-(phenylhydrazino)-2-thiazoline in 10 ml. of dry pyridine and 20 ml. of dry benzene is added dropwise 2 ml. of phenyl acetyl chloride. The resulting mixture is heated at 60°-70° C. for 30 minutes and poured into 200 ml. of water. The benzene layer is separated and the aqueous solution washed once with 20 ml. of benzene. The combined benzene solutions are washed with water and 5% sodium carbonate solution and dried with anhydrous magnesium sulfate. The benzene is evaporated to dryness and hexane is added to the residue and the resulting suspension is filtered. The solid material is washed with hexane and recrystallized from a mixture of ethyl acetate and hexane affording 2-(2-phenylacetyl-1-phenylhydrazino)-2-thiazoline, m.p. 121°-124° C.

Workup

  1. temperatureThe resulting mixture is heated at 60°-70° C. for 30 minutes
  2. additionpoured into 200 ml
  3. customThe benzene layer is separated
  4. washthe aqueous solution washed once with 20 ml
  5. washThe combined benzene solutions are washed with water and 5% sodium carbonate solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customThe benzene is evaporated to dryness and hexane
  8. additionis added to the residue
  9. filtrationthe resulting suspension is filtered
  10. washThe solid material is washed with hexane
  11. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-fff92e3163774414ab19e596caa0e6df
Source dataset
uspto-grants-1977_09
Patent number
US04046753

Reaction notes

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