Water → HCID 19973104, compound

HRID 2380320Notes

Reaction equation

HRID 2380320 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10]([F:14])([F:13])[C:11]#[N:12].P([O-])(OCC)(SCC)=[S:23].O.[ClH:32].O1CCOCC1>C(OCC)C>[ClH:32].[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C:10]([F:13])([F:14])[C:11](=[S:23])[NH2:12]

Participants

6

Reactant 4

HCID 962WaterHCID 19973111HCID 19973111, compoundHCID 204431481,4-Dioxane hydrochlorideHCID 53249491Diethyldithiophosphate

Product 1

HCID 19973104HCID 19973104, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 100 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanenitrile were added 0.2 ml of diethyl dithiophosphate and 0.04 ml of water. The resulting mixture was subjected to reaction at 80°-90° C. for 5 hours. The reaction mixture was purified by a column chromatography (eluant: chloroform/methanol=50/1) to obtain an oily matter. To the oily matter was added 0.5 ml of a 2N hydrochloric acid-dioxane solution, and then diethyl ether was added. The resulting crystals were collected by filtration to obtain 110 mg of 3-(2,4-difluorophenyl)-2,2-difluoro-3-hydroxy-4-(1H-1,2,4-triazol-1-yl)butanethioamide hydrochloride.

Workup

  1. customThe resulting mixture was subjected to reaction at 80°-90° C. for 5 hours
  2. customThe reaction mixture was purified by a column chromatography (eluant: chloroform/methanol=50/1)
  3. customto obtain an oily matter
  4. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-dfdba8fdfeb5441388970611c9ad6434
Source dataset
uspto-grants-1994_11
Patent number
US05366989

Reaction notes

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