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

HRID 867168Notes

Reaction equation

HRID 867168 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-2f44e0ca32b34601b6ac5966e3af761f
Source dataset
uspto-grants-1978_07
Patent number
US04103018

Reaction notes

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