Water → HCID 23312051, compound

HRID 745806Notes

Reaction equation

HRID 745806 reaction equation
C([O:3][C:4]([CH:6]1[O:10][C:9]2[CH:11]=[C:12]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:13]([Cl:15])=[CH:14][C:8]=2[O:7]1)=[O:5])C.NC(N)=N.O>CN(C)C=O>[Cl:15][C:13]1[C:12]([S:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:11][C:9]2[O:10][CH:6]([C:4]([OH:5])=[O:3])[O:7][C:8]=2[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3520GuanidineHCID 54288572HCID 54288572, compound

Product 1

HCID 23312051HCID 23312051, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.88 g (0.0069 mol) of 5-chloro-6-(4-chlorophenylsulphonyl)-1,3-benzodioxole-2-carboxylic acid ethyl ester are dissolved in 20 ml of dimethylformamide and are added to 0.71 g (0.012 mol) of guanidine at room temperature. The mixture is stirred for 2 hours at room temperature, then poured out onto 200 ml of water. After stirring for 1/2 hour, a crystalline suspension has formed. This is filtered, washed with water, and the crude product is dried in a vacuum drying chamber at 30°-40°. The crude product is then digested with 25 ml of ethyl acetate, partial dissolution and recrystallisation occurring. The whole is cooled for 1/2 hour in an ice-bath, filtered and dried, yielding, in the form of beige crystals, 5-chloro-6-(4-chlorophenylsulphonyl)-1,3-benzodioxole-2-carboxylic acid guanidide having a melting point of from 215° (decomposition).

Workup

  1. stirringAfter stirring for 1/2 hour
  2. customa crystalline suspension has formed
  3. filtrationThis is filtered
  4. washwashed with water
  5. dry with materialthe crude product is dried in a vacuum
  6. customdrying chamber at 30°-40°
  7. dissolutionThe crude product is then digested with 25 ml of ethyl acetate, partial dissolution and recrystallisation
  8. temperatureThe whole is cooled for 1/2 hour in an ice-bath
  9. filtrationfiltered
  10. customdried

Sources & evidence

ORD record
ord-9906d0fe00604d8f9031847706b6b124
Source dataset
uspto-grants-1986_07
Patent number
US04600709

Reaction notes

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