1H-1,2,4-Triazole → 4-Chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one naphthalene-1,5-disulphonate

HRID 127238Notes

Reaction equation

HRID 127238 reaction equation
Br[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][Cl:6].[NH:18]1[CH:22]=[N:21][CH:20]=[N:19]1.[C:23]1([S:37]([OH:40])(=[O:39])=[O:38])[C:24](S(O)(=O)=O)=[CH:25][CH:26]=[C:27]2[C:32]=1[CH:31]=[CH:30][CH:29]=[CH:28]2>C(#N)C.CC(C)=O>[C:23]1([S:37]([OH:40])(=[O:38])=[O:39])[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([S:37]([OH:40])(=[O:39])=[O:38])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[Cl:6][CH2:5][C:4]([CH3:8])([CH3:7])[C:3](=[O:9])[CH:2]([O:10][C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=1)[N:18]1[CH:22]=[N:21][CH:20]=[N:19]1

Participants

6

Reactant 3

HCID 92571H-1,2,4-TriazoleHCID 3015207Naphthalenedisulfonic acidHCID 202865621-Bromo-4-chloro-1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one

Product 1

HCID 202865774-Chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one naphthalene-1,5-disulphonateYield 192.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

268.3 g (0.79 mol) of crude 1-bromo-4-chloro-1-(4-chlorophenoxy)-3,3-dimethyl-butan-2-one were dissolved in 2 l of absolute acetonitrile. 190 g (2.7 mol) of 1,2,4-triazole were added thereto and the mixture was heated for 20 hours under reflux. It was then concentrated by distilling off the solvent in vacuo and the residue was taken up in 1,000 ml of methylene chloride. The mixture was washed three times with 250 ml of water at a time, dried over sodium sulphate and again concentrated in vacuo. The oil which remained was dissolved in 1,000 ml of acetone and a solution of 140 g (0.48 mol) of naphthalenedisulphonic acid in 500 ml of acetone was added. After 30 minutes, the resulting precipitate was filtered off. 285 g (76.6% of theory) of 4-chloro-1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one naphthalene-1,5-disulphonate of melting point 245° C. (with decomposition) were obtained.

Workup

  1. temperaturethe mixture was heated for 20 hours
  2. temperatureunder reflux
  3. concentrationIt was then concentrated
  4. distillationby distilling off the solvent in vacuo
  5. washThe mixture was washed three times with 250 ml of water at a time
  6. dry with materialdried over sodium sulphate
  7. concentrationagain concentrated in vacuo
  8. dissolutionThe oil which remained was dissolved in 1,000 ml of acetone
  9. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-5cb06980892b4e3e94355ccb305ed7cf
Source dataset
uspto-grants-1981_03
Patent number
US04255434

Reaction notes

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