Water → HCID 46846425, compound

HRID 2039662Notes

Reaction equation

HRID 2039662 reaction equation
[F:1][CH:2]([F:30])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=3[C:8]=2[C:7]([C:20]2[O:21][CH2:22][CH:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=2)=[CH:6][CH:5]=1.N12CCCC=C1CCCNC2.O>C(#N)C.C(Cl)(Cl)(Cl)Cl.N1C=CC=CC=1>[F:30][CH:2]([F:1])[O:3][C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=3[C:8]=2[C:7]([C:20]2[O:21][CH:22]=[C:23]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:24]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 20089368HCID 20089368, compoundHCID 58496331HCID 58496331, compound

Product 1

HCID 46846425HCID 46846425, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of ethyl 2-(4-(difluoromethoxy)-8-nitrodibenzo[b,d]furan-1-yl)-4,5-dihydrooxazole-4-carboxylate (0.8 g, 1.90 mmol) in acetonitrile (8 mL), CCl4 (5 mL) and pyridine (8 mL) were added. To this mixture 1,3-diaza bicyclo[5.4.0]undec-7-ene (DBU) (1.6 mL, 10.72 mmol) was added. The reaction mass was stirred at room temperature for 1 hour. The reaction mixture was poured into the cold water (50 mL) and extracted with dichloromethane (2×50 mL). The organics were dried over sodium sulphate and filtered. The organics were evaporated under reduced pressure to give the crude product. The product was purified by column chromatography by using gradient of ethyl acetate in hexane (0-5) %. Yield—94%. 1H-NMR (CDCl3) δ: 1.52-1.55 (m, 3H), 4.54-4.60 (m, 2H), 6.72-6.90-7.08 (brs, 1H), 7.51 (d, 1H), 7.77 (d, 1H), 8.14 (d, 1H), 8.46 (s, 1H), 8.52-8.55 (m, 1H), 10.66 (d, 1H); HPLC (purity): 97.4%; Mass calculated for C19H12F2N2O7-418.3, observed—419.1; Rf—0.49 (Ethyl acetate:Hexane (3:7).

Workup

  1. extractionextracted with dichloromethane (2×50 mL)
  2. dry with materialThe organics were dried over sodium sulphate
  3. filtrationfiltered
  4. customThe organics were evaporated under reduced pressure

Sources & evidence

ORD record
ord-4a4dc8f635304431abbcd0f06c8f0287
Source dataset
uspto-grants-2013_11
Patent number
US08580795B2

Reaction notes

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