HCID 53980706, compound → 60201-60-7

HRID 236984Notes

Reaction equation

HRID 236984 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([N:7]([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)[CH3:8])=[O:6]>CO.O>[F:17][C:16]([F:19])([F:18])[C:15]([C:12]1[CH:13]=[CH:14][C:9]([N:7]([C:5]2[O:6][CH2:2][CH2:3][N:4]=2)[CH3:8])=[CH:10][CH:11]=1)([OH:24])[C:20]([F:23])([F:22])[F:21]

Participants

4

Reactant 1

HCID 53980706HCID 53980706, compound

Product 1

HCID 2131494660201-60-7Yield 86.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Dissolve 10.0 g (26 m.mole) of N-(2-chloroethyl)-N'-[4-(hexafluoro-2-hydroxy-2-propyl)phenyl]-N'-methyl-urea in a mixture of 50 ml of methanol and 100 ml of water. Heat for one hour on a steam bath. Concentrate, and partition between 1N aqueous sodium bicarbonate solution and ether (diethyl) and then extract with 200 ml of 1N hydrochloric acid. Add sodium bicarbonate and then extract with 200 ml of ether. Dry the ether extract and concentrate to obtain 7.8 g of the title compound as a white solid, m.p. 188°-190° C. The salts may be prepared by standard techniques such as by treatment of a solution of the free base in a suitable organic solvent, e.g. ether, with the desired acid, e.g. hydrochloric, and then filtering off the precipitated salt. The hydrochloride salt melts at 147°-149° C.

Workup

  1. temperatureHeat for one hour on a steam bath
  2. concentrationConcentrate
  3. custompartition between 1N aqueous sodium bicarbonate solution and ether (diethyl)
  4. extractionextract with 200 ml of 1N hydrochloric acid
  5. extractionAdd sodium bicarbonate and then extract with 200 ml of ether
  6. dry with materialDry the ether
  7. extractionextract
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-a84c18e3fd9c4d7b884f2f5a674a2d76
Source dataset
uspto-grants-1979_06
Patent number
US04159335

Reaction notes

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