Ethylenediamine → HCID 23453958, compound

HRID 1706144Notes

Reaction equation

HRID 1706144 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].[CH2:20]([NH2:23])[CH2:21][NH2:22]>C1(C)C=CC=CC=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[NH:22][CH2:21][CH2:20][N:23]=4)=[CH:12][CH:11]=3)[C:6]=2[CH:18]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 5362487SulfurHCID 23453959HCID 23453959, compound

Product 1

HCID 23453958HCID 23453958, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

44 g of 5-chloro-3-(4'-chloromethylphenyl)-1,2-benzisothiazole, 9.6 g of sulfur and 18 g of ethylenediamine in 500 ml of toluene are refluxed for 20 hours. The reaction mixture is filtered hot, the filtrate is cooled and the resulting crystals are filtered off. After recrystallization from toluene in the presence of active charcoal, 26 g of 5-chloro-3-[4-(imidazolin-2-yl)-phenyl]-1,2-benzisothiazole, melting at 195° C., are obtained. The yield corresponds to 55% of theory.

Workup

  1. filtrationThe reaction mixture is filtered hot
  2. temperaturethe filtrate is cooled
  3. filtrationthe resulting crystals are filtered off
  4. customAfter recrystallization from toluene in the presence of active charcoal, 26 g of 5-chloro-3-[4-(imidazolin-2-yl)-phenyl]-1,2-benzisothiazole, melting at 195° C.
  5. customare obtained

Sources & evidence

ORD record
ord-989775efa0574a26901363402259679b
Source dataset
uspto-grants-1980_06
Patent number
US04206217

Reaction notes

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