Water → HCID 1186353, compound

HRID 904081Notes

Reaction equation

HRID 904081 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:11][C:12]([F:27])([F:26])[C:13]([C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=1)([OH:18])[C:14]([F:17])([F:16])[F:15].O>N1C=CC=CC=1>[F:11][C:12]([F:26])([F:27])[C:13]([C:19]1[CH:25]=[CH:24][C:22]([NH:23][S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:21][CH:20]=1)([OH:18])[C:14]([F:15])([F:17])[F:16]

Participants

5

Reactant 3

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 1186353HCID 1186353, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Add 4.22 g (24 mmole) of benzenesulfonyl chloride dropwise to 5.18 g (20 mmole) of 4-(hexafluoro-2-hydroxy-2-propyl)aniline in 25 ml of pyridine and heat to 100° C. for 8 hours. Pour the reaction into H2O and extract with Et2O. Wash with 1N HCl and extract with 1H NaOH. Acidify the NaOH and extract with Et2O. Dry, concentrate and recrystallize from Et2O and hexane to obtain 4'-(hexafluoro-2-hydroxy-2-propyl)-benzenesulfonanilide; m.p. 117°-118° C.

Workup

  1. additionPour
  2. extractionextract with Et2O
  3. washWash with 1N HCl
  4. extractionextract with 1H NaOH
  5. extractionextract with Et2O
  6. customDry
  7. concentrationconcentrate
  8. customrecrystallize from Et2O and hexane

Sources & evidence

ORD record
ord-8e72d9ebf44b4614b80cfb1cced027ee
Source dataset
uspto-grants-1980_10
Patent number
US04230635

Reaction notes

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