2,2,2-Trifluoroethanol → 3-Nitro-5-sulphamyl-4-(beta,beta,beta-trifluoroethoxy)-benzoic acid

HRID 1287755Notes

Reaction equation

HRID 1287755 reaction equation
Cl[C:2]1[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[N+:15]([O-:17])=[O:16].[F:18][C:19]([F:23])([F:22])[CH2:20][OH:21]>>[N+:15]([C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([S:11](=[O:14])(=[O:13])[NH2:12])[C:2]=1[O:21][CH2:20][C:19]([F:23])([F:22])[F:18])[C:6]([OH:8])=[O:7])([O-:17])=[O:16]

Participants

3

Reactant 2

HCID 64092,2,2-TrifluoroethanolHCID 898934-Chloro-3-nitro-5-sulphamoylbenzoic acid

Product 1

HCID 215059913-Nitro-5-sulphamyl-4-(beta,beta,beta-trifluoroethoxy)-benzoic acid

Procedure

To a solution of sodium β,β,β -trifluoroethoxide in β,β,β-trifluoroethanol (prepared by dissolving 2.1 g of sodium in 45 ml of β,β,β-trifluoroethanol), 4-chloro-3-nitro-5-sulphamyl-benzoic acid (4.2 g) was added, and the resulting solution was refluxed for 5 days. After evaporation of the reaction mixture in vacuo, water (50 ml) was added, and the aqueous solution was acidified with 4N hydrochloric acid. After standing in a refrigerator, the precipitate was collected by suction. After several recrystallizations from aqueous ethanol, the 3-nitro-5-sulphamyl-4-(β,β,β-trifluoroethoxy)-benzoic acid was obtained with a melting point of 195°-197° C.

Workup

  1. temperaturethe resulting solution was refluxed for 5 days
  2. customAfter evaporation of the reaction mixture in vacuo, water (50 ml)
  3. additionwas added
  4. customthe precipitate was collected by suction
  5. customAfter several recrystallizations from aqueous ethanol

Sources & evidence

ORD record
ord-3cb5a802db2441dbbb7cac444b3fa5db
Source dataset
uspto-grants-1976_10
Patent number
US03985777

Reaction notes

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