2,4-Difluorophenyl isocyanate → HCID 86746453, compound

HRID 1645887Notes

Reaction equation

HRID 1645887 reaction equation
[NH2:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:20])[CH:3]=1.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[N:29]=[C:30]=[O:31]>C1(C)C=CC=CC=1>[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[NH:29][C:30]([NH:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]([O:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:15])([CH3:16])[C:11]([O:13][CH3:14])=[O:12])=[C:4]([CH3:20])[CH:3]=1)=[O:31]

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 15068117HCID 15068117, compound

Product 1

HCID 86746453HCID 86746453, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

5-(4-Amino-2,5-dimethylphenoxy)-2,2-dimethylpentanoic acid, methyl ester as the free base (Example 2) (4.15 g, 15 mmol) in 50 mL of toluene, 2.33 g (15 mmol) of 2,4-difluorophenyl isocyanate is added and the solution is stirred at 50° C. for 18 hours overnight. The solid mixture is evaporated on a rotary evaporator; the precipitate is taken up in acetonitrile, treated with charcoal, filtered, evaporated, and the residual, crystalline precipitate is recrystallized from 70 mL of toluene: 50 mL of isooctane to afford 5.7 g of the title compound as a slight pink solid; mp 152°-153° C.

Workup

  1. customThe solid mixture is evaporated on a rotary evaporator
  2. additiontreated with charcoal
  3. filtrationfiltered
  4. customevaporated
  5. customthe residual, crystalline precipitate is recrystallized from 70 mL of toluene

Sources & evidence

ORD record
ord-0a1cd8fc375341b7806bfd1f00937351
Source dataset
uspto-grants-1993_01
Patent number
US05177106

Reaction notes

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