Propylenediamine → HCID 20337370, compound

HRID 1706143Notes

Reaction equation

HRID 1706143 reaction equation
[Cl:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][N:10]=2)=[CH:5][CH:4]=1.[S].[NH2:19][CH2:20][CH:21]([NH2:23])C.[CH3:24]OCCO>>[ClH:1].[CH3:24][N:23]1[CH2:21][CH2:20][N:19]=[C:2]1[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[S:11][N:10]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 4

HCID 6567PropylenediamineHCID 80192-MethoxyethanolHCID 5362487SulfurHCID 23453963HCID 23453963, compound

Product 1

HCID 20337370HCID 20337370, compound

Procedure

26 g of 3-(4'-chloromethylphenyl)-1,2-benzisothiazole, 6.4 g of sulfur and 15 g of 1,2-diaminopropane in 400 ml of glycol monomethyl ether are heated for 15 hours at 110° C. After distilling off the solvent, the residue is dissolved in 50 g of methanol and this solution is stirred into 400 g of ethereal hydrochloric acid (15 g of HCl in diethyl ether), whilst cooling. The crystals formed are filtered off and dissolved in 300 parts of water, the solution is filtered and the filtrate is rendered alkaline with concentrated NaOH and extracted with methylene chloride. The methylene chloride phase is dried and 20 g of hydrogen chloride gas are passed in. 17 g of the desired end product are obtained as colorless crystals, melting at 243° C. The yield corresponds to 52% of theory.

Workup

  1. distillationAfter distilling off the solvent
  2. dissolutionthe residue is dissolved in 50 g of methanol
  3. temperaturewhilst cooling
  4. customThe crystals formed
  5. filtrationare filtered off
  6. dissolutiondissolved in 300 parts of water
  7. filtrationthe solution is filtered
  8. extractionextracted with methylene chloride
  9. dry with materialThe methylene chloride phase is dried
  10. custom17 g of the desired end product are obtained as colorless crystals, melting at 243° C

Sources & evidence

ORD record
ord-3b11ff29f04244a3af528eebc6d63190
Source dataset
uspto-grants-1980_06
Patent number
US04206217

Reaction notes

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