1,5-Naphthalenedisulfonic acid → 2-Acetoxy-3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butane 1,5-naphthalenedisulphonate

HRID 1649179Notes

Reaction equation

HRID 1649179 reaction equation
[F:1][CH2:2][C:3]([CH2:21][F:22])([CH3:20])[CH:4]([OH:19])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[C:23]1([S:37]([OH:40])(=[O:39])=[O:38])[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([S:33]([OH:36])(=[O:35])=[O:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[C:41](OC(=O)C)(=[O:43])[CH3:42]>CC(C)=O>[C:23]1([S:37]([OH:40])(=[O:39])=[O:38])[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([S:33]([OH:36])(=[O:35])=[O:34])[C:27]=2[CH:26]=[CH:25][CH:24]=1.[C:41]([O:19][CH:4]([C:3]([CH2:21][F:22])([CH2:2][F:1])[CH3:20])[CH:5]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[N:6]1[CH:10]=[CH:9][N:8]=[CH:7]1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 66661,5-Naphthalenedisulfonic acidHCID 7918Acetic AnhydrideHCID 130194383,3-Bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-ol

Product 1

HCID 129066522-Acetoxy-3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butane 1,5-naphthalenedisulphonateYield 68%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

12.2 g (0.037 mol) of 3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butan-2-ol were dissolved in 70 ml of acetic anhydride. The solution was stirred at 100° C. for 16 hours, the excess acetic anhydride was distilled off in vacuo and the residue was taken up in 300 ml of methylene chloride. The organic phase was washed twice with 800 ml of water each time, dried over sodium sulphate and concentrated. The residue was taken up in 100 ml of acetone, and a solution of 9 g (0.038 mol) of 1,5-naphthalenedisulphonic acid in 50 ml of acetone was added. After 2 hours, the precipitate which had formed was filtered off and dried. 13 g (68% of theory) of 2-acetoxy-3,3-bisfluoromethyl-1-(4-chlorophenoxy)-1-(imidazol-1-yl)-butane 1,5-naphthalenedisulphonate of melting point 221°-224° C. were obtained.

Workup

  1. distillationthe excess acetic anhydride was distilled off in vacuo
  2. washThe organic phase was washed twice with 800 ml of water each time
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated
  5. waitAfter 2 hours
  6. customthe precipitate which had formed
  7. filtrationwas filtered off
  8. customdried

Sources & evidence

ORD record
ord-248ea964dd034f58b3a3318b904d5b8c
Source dataset
uspto-grants-1983_11
Patent number
US04415586

Reaction notes

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