Toluene → HCID 20337373, compound

HRID 1706145Notes

Reaction equation

HRID 1706145 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([CH2:16]Cl)=[CH:12][CH:11]=3)[C:6]=2[CH:18]=1.[S].[NH2:20][CH2:21][CH:22]([NH2:24])C.[C:25]1(C)C=CC=CC=1>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[N:20]([CH3:25])[CH2:21][CH2:22][N:24]=4)=[CH:12][CH:11]=3)[C:6]=2[CH:18]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 6567PropylenediamineHCID 5362487SulfurHCID 23453959HCID 23453959, compound

Product 1

HCID 20337373HCID 20337373, compound

Procedure

44 g of 5-chloro-3-(4'-chloromethylphenyl)-1,2-benzisothiazole, 9.6 g of sulfur and 22.5 g of 1,2-diaminopropane in 600 ml of toluene are refluxed for 24 hours. The reaction mixture is filtered hot and the filtrate is concentrated on a rotary evaporator. The residue is dissolved in 500 ml of ether and 30 g of hydrogen chloride gas are passed into the solution, whilst cooling. The resulting crystals are filtered off and recrystallized from water. 31 g of product melting, with decomposition, at 248° C., are obtained. The yield corresponds to 57% of theory.

Workup

  1. filtrationThe reaction mixture is filtered hot
  2. concentrationthe filtrate is concentrated on a rotary evaporator
  3. dissolutionThe residue is dissolved in 500 ml of ether
  4. temperaturewhilst cooling
  5. filtrationThe resulting crystals are filtered off
  6. customrecrystallized from water
  7. custommelting, with decomposition, at 248° C.
  8. customare obtained

Sources & evidence

ORD record
ord-d49abace2b684cd4bae6645dc289d028
Source dataset
uspto-grants-1980_06
Patent number
US04206217

Reaction notes

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