HCID 12880033, compound → HCID 12880036, compound

HRID 2287040Notes

Reaction equation

HRID 2287040 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[O:5][CH:6]([C:8]1[S:12][C:11]([NH:13][C:14](=[O:23])[N:15]([CH2:17][CH:18](OC)[O:19]C)[CH3:16])=[N:10][N:9]=1)[CH3:7]>O.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][C:26]=1[Cl:27])[O:5][CH:6]([C:8]1[S:12][C:11]([N:13]2[CH:18]([OH:19])[CH2:17][N:15]([CH3:16])[C:14]2=[O:23])=[N:10][N:9]=1)[CH3:7]

Participants

4

Reactant 1

HCID 12880033HCID 12880033, compound

Product 1

HCID 12880036HCID 12880036, compoundYield 109%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution containing 4.0 grams of the 3-[5-[1-(3,4-dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-(2,2-dimethoxyethyl)urea (prepared above) in 200 milliliters of water and 2 milliliters of concentrated hydrochloric acid (HCl) was refluxed for 165 minutes, cooled and then extracted with chloroform CHCl3, and phase separated. The organic phase was dried over MgSO4, filtered, and topped in a roto-vac at 70° C. to yield 3.9 grams of a viscous oil. The viscous oil was dissolved in 20 milliliters of diethylether, and the solution crystallized. The crystals were removed by suction filter, and were dried in a vacuum oven at 80° C. to yield 1.9 grams of white crystals of 3-[5-[1-(3,4-dichlorophenoxy)ethyl]-1,3,4-thiadiazol-2-yl]-1-methyl-4-hydroxy-2-imidazolidinone with a (Melting point 135°-138° C.) and

Workup

  1. temperaturewas refluxed for 165 minutes
  2. temperaturecooled
  3. extractionextracted with chloroform CHCl3, and phase
  4. customseparated
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customtopped in a roto-vac at 70° C.

Sources & evidence

ORD record
ord-8b9e6b6e265a469392ae85dcfac5c5c2
Source dataset
uspto-grants-1981_05
Patent number
US04268675

Reaction notes

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