Hydrochloric Acid → HCID 70873787, compound

HRID 2172247Notes

Reaction equation

HRID 2172247 reaction equation
Cl.[N:2]([C:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)([CH3:7])[CH3:6])=C=O>C(O)(=O)C>[CH3:7][C:5]([NH2:2])([C:8]1[CH:9]=[CH:10][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:23])[F:24])=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[CH3:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86709391HCID 86709391, compound

Product 1

HCID 70873787HCID 70873787, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Concentrated hydrochloric acid (18 ml) was added to an acetic acid solution (24 ml) of 1-(2-isocyanatopropan-2-yl)-4-[4-(trifluoromethyl)benzyloxy]benzene (4.35 g, 13.0 mmol) and stirred at room temperature. After 2.5 hours, the mixture was heated to 80° C. and stirred for 1 hour. The solvent was then distilled off. Ice and a 5 N sodium hydroxide aqueous solution were sequentially added to the residue and stirred, followed by extraction with ethyl acetate. The resultant was washed with a saturated sodium chloride aqueous solution and dried over sodium sulfate. After removing the desiccant by filtration, the solvent was distilled off to afford the title compound as a brown solid (3.3 g, 82%).

Workup

  1. temperaturethe mixture was heated to 80° C.
  2. stirringstirred for 1 hour
  3. distillationThe solvent was then distilled off
  4. additionIce and a 5 N sodium hydroxide aqueous solution were sequentially added to the residue
  5. stirringstirred
  6. extractionfollowed by extraction with ethyl acetate
  7. washThe resultant was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over sodium sulfate
  9. customAfter removing the
  10. filtrationdesiccant by filtration
  11. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-b0a84141eb7c4e05b97a1181a7277528
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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