3,4,5,6-Tetrahydrophthalic anhydride → HCID 51353550, compound

HRID 2093290Notes

Reaction equation

HRID 2093290 reaction equation
[NH2:1][C:2]1[C:17]([F:18])=[CH:16][C:5]2[O:6][C:7]([F:15])([F:14])[C:8](=[O:13])[N:9]([CH2:10][C:11]#[CH:12])[C:4]=2[CH:3]=1.[C:19]1(=O)[C:27]2[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=2[C:21](=[O:28])[O:20]1>C(O)(=O)C>[F:15][C:7]1([F:14])[C:8](=[O:13])[N:9]([CH2:10][C:11]#[CH:12])[C:4]2[CH:3]=[C:2]([N:1]3[C:19](=[O:20])[C:27]4[CH2:26][CH2:25][CH2:24][CH2:23][C:22]=4[C:21]3=[O:28])[C:17]([F:18])=[CH:16][C:5]=2[O:6]1

Participants

4

Reactant 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 866695376-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 51353550HCID 51353550, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

6-amino-2,2,7-trifluoro-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (20 g, 78 mmol) and 4,5,6,7-tetrahydroisobenzofuran-1,3-dione (12.47 g, 82 mmol) in acetic acid (500 ml) were stirred at 120° C. overnight, after which time tlc (thin layer chromatography) analysis indicated that the reaction was complete. The reaction mixture was concentrated in vacuo and triturated with toluene to yield 34.6 g of crude product. This material was combined with a further quantity (6.23 g) of crude product which had been obtained in a similar manner, and the combined product was coated on isolute absorbens (˜70 g). Filtration over silica afforded 2 fractions: F1: 12.9 g and F2: 19.35 g. Both fractions were triturated with di-isopropyl ether to yield: T1: 6.04 g (88% purity) and T2: 14.7 g (>95% purity). T1 was recrystallised from MeOH to yield a further 4.65 g of product (>95% purity).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customtriturated with toluene
  3. customto yield 34.6 g of crude product
  4. customhad been obtained in a similar manner
  5. filtrationFiltration over silica
  6. customafforded 2 fractions
  7. customBoth fractions were triturated with di-isopropyl ether to yield
  8. customT1 was recrystallised from MeOH

Sources & evidence

ORD record
ord-3f1419f31d4c4cb39a594075805ee05b
Source dataset
uspto-grants-2013_05
Patent number
US08445407B2

Reaction notes

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