Tetrahydrofuran → 1(3H)-Isobenzofuranone, 6-fluoro-3-((1-methyl-1H-1,2,4-triazol-5-yl)methylene)-4-nitro-, (3Z)-

HRID 1617264Notes

Reaction equation

HRID 1617264 reaction equation
[CH2:1]1COCC1.Cl.[F:7][C:8]1[CH:9]=[C:10]([N+:27]([O-:29])=[O:28])[C:11]([C:18](=[O:26])[CH2:19][C:20]2[N:24]=[CH:23][N:22](C)[N:21]=2)=[C:12]([CH:17]=1)[C:13](OC)=[O:14]>CCCCCCC>[F:7][C:8]1[CH:17]=[C:12]2[C:11](/[C:18](=[CH:19]/[C:20]3[N:21]([CH3:1])[N:22]=[CH:23][N:24]=3)/[O:26][C:13]2=[O:14])=[C:10]([N+:27]([O-:29])=[O:28])[CH:9]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 67355822methyl 5-fluoro-2-(2-(1-methyl-1H-1,2,4-triazole-3-yl)acetyl)-3-nitrobenzoate hydrochloride

Product 1

HCID 533535091(3H)-Isobenzofuranone, 6-fluoro-3-((1-methyl-1H-1,2,4-triazol-5-yl)methylene)-4-nitro-, (3Z)-

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

An alternative workup procedure to that illustrated in Example 2A follows. Instead of evaporating the reaction mixture to dryness, it was condensed to 2 volumes, followed by solvent exchange with 12 volumes of THF, and then 12 volumes of heptane. The slurry mixture was concentrated to 2 volumes and filtered to give the product. As such, 1.8 kilograms of (Z)-6-fluoro-3-((1-methyl-1H-1,2,4-triazol-3-yl)methylene)-4-nitroisobenzofuran-1(3H)-one (3) gave 2.15 kilograms (yield 96.4%) of the product methyl 5-fluoro-2-(2-(1-methyl-1H-1,2,4-triazole-3-yl)acetyl)-3-nitrobenzoate hydrochloride (4).

Workup

  1. customInstead of evaporating the reaction mixture to dryness, it
  2. customcondensed to 2 volumes
  3. concentrationThe slurry mixture was concentrated to 2 volumes
  4. filtrationfiltered
  5. customto give the product

Sources & evidence

ORD record
ord-e9119e1a6c8a4afabf571253f792f17f
Source dataset
uspto-grants-2014_07
Patent number
US08765945B2

Reaction notes

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