Hydrochloric Acid → HCID 178477323, compound

HRID 542504Notes

Reaction equation

HRID 542504 reaction equation
C(O[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.[CH2:24]([SH:26])[CH3:25]>CCOCC.C(#N)C>[Cl:21][C:17]1[CH:16]=[C:15]([NH:14][C:12]([NH:11][C:8]2[N:9]([CH3:10])[CH:5]([S:26][CH2:24][CH3:25])[C:6](=[O:22])[N:7]=2)=[O:13])[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 178475628HCID 178475628, compound

Product 1

HCID 178477323HCID 178477323, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 3.00 g (9.20 mmol) of N-(5-acetyloxy-4,5-dihydro-1-methyl-4-oxo-1H-imidazol-2-yl)-N'-(3-chlorophenyl)urea, the compound of Example 1a, in 75 ml of anhydrous ether was treated with anhydrous HCl until no more precipitation occurred. The solid was filtered, washed with anhydrous ether and suspended in a mixture of 1.8 ml (25 mmol) of ethyl mercaptan and 30 ml of acetonitrile. After heating under reflux for 1 hr, the reaction mixture was evaporated in vacuo. The crystalline residue was 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/water afforded 2.20 g (73%) of the title compound. Recrystallization from ether/hexane and finally ethanol/water gave an analytical sample mp 102°-104° C.

Workup

  1. filtrationThe solid was filtered
  2. washwashed with anhydrous ether
  3. temperatureAfter heating
  4. temperatureunder reflux for 1 hr
  5. customthe reaction mixture was evaporated in vacuo
  6. dissolutionThe crystalline residue was dissolved in THF/water
  7. extractionextracted with ether
  8. washThe combined ether layers were washed with water to pH 5-6
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customCrystallization of the residue from methanol/water

Sources & evidence

ORD record
ord-100a222c49f1430d9e11de67488c96d8
Source dataset
uspto-grants-1987_04
Patent number
US04657922

Reaction notes

Loading…