Toluene → HCID 22558978, compound

HRID 2378557Notes

Reaction equation

HRID 2378557 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([O:14][CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=[C:10]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])[CH:9]=2)=[CH:4][C:3]=1[CH3:26].[N:27]([O-])=O.[Na+].NC(N)=O.C1(C)C=CC=CC=1>C(O)(=O)C.O>[CH:15]1([O:14][C:13]2[CH:12]=[CH:11][C:10]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:9][C:8]=2[C:5]2[CH:4]=[C:3]3[C:2](=[CH:7][CH:6]=2)[NH:1][N:27]=[CH:26]3)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 1176UreaHCID 23668193Sodium NitriteHCID 68742716HCID 68742716, compound

Product 1

HCID 22558978HCID 22558978, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of Intermediate 72 (760 mg) in acetic acid (4 ml) was added with an aqueous solution (0.7 ml) of sodium nitrite (156 mg) under ice cooling, and stirred for 30 minutes. This reaction mixture was added with urea (350 mg), warmed to room temperature, stirred for 30 minutes, then added with toluene (8 ml) and water (4 ml), and further stirred for 60 hours. The reaction mixture was extracted with toluene (50 ml×2). The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1) to obtain the title compound (Compound No. V-57, 411 mg).

Workup

  1. stirringstirred for 30 minutes
  2. stirringfurther stirred for 60 hours
  3. extractionThe reaction mixture was extracted with toluene (50 ml×2)
  4. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate, and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-bcdb3ed9c688410381e14a4e002c314f
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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