Potassium tert-butoxide → 2-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)anilino]-1,3-oxazol-4-one

HRID 47017Notes

Reaction equation

HRID 47017 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([OH:24])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=1)=[O:7])=[O:4].CC(C)([O-])C.[K+]>C(COC)OC>[F:17][C:16]([F:19])([F:18])[C:15]([C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:6]2[O:7][CH2:2][C:3](=[O:4])[N:5]=2)=[CH:10][CH:11]=1)([OH:24])[C:20]([F:23])([F:22])[F:21]

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 538815481-(2-Chloroacetyl)-3-[4-(hexafluoro-2-hydroxy-2-propyl)phenyl] urea

Product 1

HCID 1785169042-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)anilino]-1,3-oxazol-4-one

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To 1-(2-chloroacetyl)-3-[4-(hexafluoro-2-hydroxy-2-propyl)phenyl] urea (9.7 gm., 0.026 mole) in dimethoxyethane (500 ml) add potassium t-butoxide (5.7 gm., 0.051 mole). Stir 16 hr., concentrate, add water, acidify with conc. HCl, neutralize with sodium bicarbonate and extract with ether. Dry, concentrate, and recrystallize the residue from ether, to obtain the product, m.p. 272°-274° C.

Workup

  1. concentration, concentrate
  2. additionadd water
  3. extractionextract with ether
  4. customDry
  5. concentrationconcentrate
  6. customrecrystallize the residue from ether
  7. customto obtain the product, m.p. 272°-274° C.

Sources & evidence

ORD record
ord-f1f68e208cf4429db83624ee408fdea9
Source dataset
uspto-grants-1979_11
Patent number
US04176120

Reaction notes

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