Hydrochloric Acid → 4-Acetamido-4'-(hexafluoro-2-hydroxy-2-propyl)benzenesulfonanilide

HRID 904084Notes

Reaction equation

HRID 904084 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].[C:18]([NH:21][C:22]1[CH:31]=[CH:30][C:25]([S:26](Cl)(=[O:28])=[O:27])=[CH:24][CH:23]=1)(=[O:20])[CH3:19].Cl>N1C=CC=CC=1>[C:18]([NH:21][C:22]1[CH:23]=[CH:24][C:25]([S:26]([NH:13][C:12]2[CH:14]=[CH:15][C:9]([C:3]([OH:8])([C:4]([F:6])([F:5])[F:7])[C:2]([F:16])([F:17])[F:1])=[CH:10][CH:11]=2)(=[O:28])=[O:27])=[CH:30][CH:31]=1)(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8481N-Acetylsulfanilyl chlorideHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 233334974-Acetamido-4'-(hexafluoro-2-hydroxy-2-propyl)benzenesulfonanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To 8.5 g (36 mmole) 4-(hexafluoro-2-hydroxy-2-propyl)aniline in 30 ml pyridine, add 7.8 g (30 mmole) N-acetylsulfanilyl chloride. Stir 2 hours, pour onto ice and acidify with concentrated HCl. Extract with Et2O, and wash this with 1N NaOH. Acidify the aqueous layer, extract with Et2O and dry and concentrate. Recrystallize from Et2O-hexane to give the product; m.p. 198°-200° C.

Workup

  1. additionpour onto ice
  2. extractionExtract with Et2O
  3. washwash this with 1N NaOH
  4. extractionextract with Et2O
  5. customdry
  6. concentrationconcentrate
  7. customRecrystallize from Et2O-hexane
  8. customto give the product

Sources & evidence

ORD record
ord-8accf66319074438b47c2d124d5a8af6
Source dataset
uspto-grants-1980_10
Patent number
US04230635

Reaction notes

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