Benzylamine → 4-Benzylamino-6-(1,2,2-trichlorovinyl)-1,3-benzenedi-sulfonamide

HRID 461768Notes

Reaction equation

HRID 461768 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([Cl:12])=[C:9]([Cl:11])[Cl:10])[C:5]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:4][C:3]=1[S:17]([NH2:20])(=[O:19])=[O:18].[CH2:21]([NH2:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)(=O)C>[CH2:21]([NH:28][C:2]1[CH:7]=[C:6]([C:8]([Cl:12])=[C:9]([Cl:11])[Cl:10])[C:5]([S:13]([NH2:16])(=[O:15])=[O:14])=[CH:4][C:3]=1[S:17]([NH2:20])(=[O:19])=[O:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 213924354-Bromo-6-trichlorovinyl-1,3-benzenedisulfonamide

Product 1

HCID 213924224-Benzylamino-6-(1,2,2-trichlorovinyl)-1,3-benzenedi-sulfonamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 0.31 g. of 4-bromo-6-trichlorovinyl-1,3-benzenedisulfonamide and 0.76 ml. of benzylamine is stirred at 100° C for 2 hours and then added to 25 ml. of aqueous acetic acid and cooled in ice. A precipitate is collected by filtration which weighs 0.26 g. after drying, which gives after recrystallization from a ethylacetate/benzene/petroleum benzene mixture 0.17 g. of 4-benzylamino-6-(1,2,2-trichlorovinyl)-1,3-benzenedisulfonamide with m.p. 188°-190° C.

Workup

  1. additionA mixture of 0.31 g
  2. additionadded to 25 ml
  3. filtrationA precipitate is collected by filtration which
  4. customafter drying
  5. customwhich gives
  6. customafter recrystallization from a ethylacetate/benzene/petroleum benzene mixture 0.17 g

Sources & evidence

ORD record
ord-cd73806467c740338ba7fc85cba59835
Source dataset
uspto-grants-1977_12
Patent number
US04064239

Reaction notes

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