Triethylamine → N-[4-(hexafluoro-2-hydroxy-2-propyl)phenyl]-N'-ethylsulfamide

HRID 904083Notes

Reaction equation

HRID 904083 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].[CH2:18]([NH:20][S:21](Cl)(=[O:23])=[O:22])[CH3:19].CCN(CC)CC>C(Cl)(Cl)Cl>[F:1][C:2]([F:16])([F:17])[C:3]([C:9]1[CH:15]=[CH:14][C:12]([NH:13][S:21]([NH:20][CH2:18][CH3:19])(=[O:23])=[O:22])=[CH:11][CH:10]=1)([OH:8])[C:4]([F:6])([F:5])[F:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5778012-(4-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 11040810Ethylsulfamoyl chloride

Product 1

HCID 54217972N-[4-(hexafluoro-2-hydroxy-2-propyl)phenyl]-N'-ethylsulfamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To 5.18 g (20 mmole) 4-(hexafluoro-2-hydroxy-2-propyl)aniline and 3.44 g (24 mmole) N-ethylsulfamoyl chloride in 30 ml CHCl3, add 2.18 g (24 mmole) Et3N in 20 ml CHCl3 and stir for 16 hours. Dilute with CHCl3 and wash with 1N HCl. Dry, concentrate and recrystallize from Et2O-hexane to yield the product; m.p. 178°-179° C.

Workup

  1. washwash with 1N HCl
  2. customDry
  3. concentrationconcentrate
  4. customrecrystallize from Et2O-hexane
  5. customto yield the product

Sources & evidence

ORD record
ord-8f69a1c90b034d4ab2299814b7828bae
Source dataset
uspto-grants-1980_10
Patent number
US04230635

Reaction notes

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