Hydrochloric Acid → HCID 178493934, compound

HRID 542505Notes

Reaction equation

HRID 542505 reaction equation
[C:1]([O:4][CH:5]1[N:9]([CH3:10])[C:8]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=2)=[O:13])=[N:7][C:6]1=[O:22])(=O)C.Cl>CCOCC.C1COCC1.O>[Cl:21][C:17]1[CH:16]=[C:15]([NH:14][C:12]([NH:11][C:8]2[N:9]([CH3:10])[CH:5]([O:4][CH3:1])[C:6](=[O:22])[N:7]=2)=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178475628HCID 178475628, compound

Product 1

HCID 178493934HCID 178493934, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

A solution of 10.00 g (0.031 mol) of N-(5-acetyloxy-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl)-N'-(3-chlorophenyl) urea. The compound from Example 1a, in 200 ml of anhydrous ether was treated with anhydrous HCl until no more precipitation occurred. The solid was filtered, with anhydrous ether and dissolved in 200 ml of warm (70° C.) methanol. The reaction mixture was cooled to room temperature and after 1 hr filtered. Concentration of the filtrate gave additional material which was combined with the first crop, dissolved in THF/water and extracted with ether. The combined ether layers were washed with water to pH 5-6, dried (MgSO4) and evaporated in vacuo. Crystallization of the residue from methanol and finally methanol/pentane (5:1) afforded 3.22 g (37%) of the title compound, mp 147°-149° C.

Workup

  1. filtrationThe solid was filtered, with anhydrous ether
  2. dissolutiondissolved in 200 ml
  3. temperatureThe reaction mixture was cooled to room temperature and after 1 hr
  4. filtrationfiltered
  5. customConcentration of the filtrate gave additional material which
  6. extractionextracted with ether
  7. washThe combined ether layers were washed with water to pH 5-6
  8. dry with materialdried (MgSO4)
  9. customevaporated in vacuo
  10. customCrystallization of the residue from methanol and finally methanol/pentane (5:1)

Sources & evidence

ORD record
ord-71bdaf84aab040f7bfd5f98e87509009
Source dataset
uspto-grants-1987_04
Patent number
US04657922

Reaction notes

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