Phosphorus oxychloride → HCID 68617784, compound

HRID 1241928Notes

Reaction equation

HRID 1241928 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C@@H:10]([CH3:14])[C:11]([NH2:13])=O.O=P(Cl)(Cl)Cl>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C@@:9]([OH:21])([CH2:15][N:16]1[CH:20]=[N:19][CH:18]=[N:17]1)[C@H:10]([CH3:14])[C:11]#[N:13]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychloride2×HCID 58224182(αR,βR)-β-(2,5-Difluorophenyl)-β-hydroxy-α-methyl-1H-1,2,4-triazole-1-butanamide

Product 1

HCID 68617784HCID 68617784, compoundYield 185.1%

Procedure

5.8 g (20 mmol) of (2R,3R)-3-(2,5-difluoro-phenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-yl-butyramide were heated with 7.3 ml (78 mmol) of POCl3 at 40° C. for 3 hours. After cooling to room temperature the excess POCl3 was evaporated at reduced pressure to yield crude 10.3 g of (2R,3R)-3-(2,5-difluorophenyl)-3-hydroxy-2-methyl-4-[1,2,4]triazol-1-yl-butyronitrile which was used directly in the next step (Example 14).

Workup

  1. customwas evaporated at reduced pressure

Sources & evidence

ORD record
ord-9e46939dbe1b4dc9b2301802b6028f35
Source dataset
uspto-grants-2006_10
Patent number
US07115643B2

Reaction notes

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