Water → HCID 22624543, compound

HRID 279166Notes

Reaction equation

HRID 279166 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[N:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])=[CH:16][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:34](Cl)(=[O:42])[O:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>C(OCC)(=O)C.O1CCCC1>[O:13]=[C:12]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:34](=[O:42])[O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:7][CH:6]=2)[N:9]=[CH:10][N:11]1[C:14]1[CH:15]=[CH:16][C:17]([O:20][CH2:21][C:22]([F:26])([F:27])[CH:23]([F:24])[F:25])=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 15891Phenyl chloroformateHCID 22624530HCID 22624530, compound

Product 1

HCID 22624543HCID 22624543, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent3×

Procedure

2-(4-Aminophenyl)-4-[4-(2,2,3,3-tetrafluoropropoxy) phenyl]-3(2H,4H)-1,2,4-triazolone (4.6 g) and pyridine (1.43 g) were dissolved in ethyl acetate (200 ml). To the resultant was added dropwise at room temperature a solution of phenyl chlorocarbonate (2.83 g) in ethyl acetate (20 ml). After the addition was completed, the reaction solution was stirred at room temperature for 2 hours. Water (200 ml), ethyl acetate (600 ml) and tetrahydrofuran (300 ml) were added thereto. The separated organic layer was washed with 5% phosphoric acid (200 ml×2) and water (200 ml) successively, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated to about 50 ml and the precipitated crystals were collected by filtration. The crystals thus obtained were washed with diethyl ether and dried to give phenyl 4-[5-oxo-4-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-1H,4H-1,2,4-triazol-1-yl]phenylcarbamate (5.6 g, 93%) as colorless scaly crystals.

Workup

  1. additionAfter the addition
  2. washThe separated organic layer was washed with 5% phosphoric acid (200 ml×2) and water (200 ml) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated to about 50 ml
  6. filtrationthe precipitated crystals were collected by filtration
  7. customThe crystals thus obtained
  8. washwere washed with diethyl ether
  9. customdried

Sources & evidence

ORD record
ord-24f949183524472c9b5428faae92902a
Source dataset
uspto-grants-2002_03
Patent number
US06362206B1

Reaction notes

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