Water → HCID 68457779, compound

HRID 2197917Notes

Reaction equation

HRID 2197917 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[C:21]([Si:25]([CH3:35])([CH3:34])[O:26][C:27]1[CH:28]=[C:29]([NH2:33])[CH:30]=[CH:31][CH:32]=1)([CH3:24])([CH3:23])[CH3:22].C(N(CC)C(C)C)(C)C.O>C1COCC1>[C:21]([Si:25]([CH3:35])([CH3:34])[O:26][C:27]1[CH:28]=[C:29]([NH:33][C:10](=[O:11])[C:9]2[CH:13]=[CH:14][CH:15]=[C:7]([O:6][C:5]3[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][C:4]=3[N+:18]([O-:20])=[O:19])[CH:8]=2)[CH:30]=[CH:31][CH:32]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 143147823-((Tert-butyldimethylsilyl)oxy)anilineHCID 866155003-(4-Chloro-2-nitro-phenoxy)-benzoyl chloride

Product 1

HCID 68457779HCID 68457779, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product from Example 168b (1.3 g, 4.2 mmol) in THF (25 mL) was added 3-(tert-Butyl-dimethyl-silanyloxy)-phenylamine (1.0 g, 4.2 mmol), and N,N-diisopropylethylamine (0.67 g, 5.2 mmol). The reaction was stirred for 16 h. The reaction was poured into water and extracted with ethyl acetate. The organic layer washed with 5% HCL, water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (1.3 g, 85%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer washed with 5% HCL, water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ff081b209efa4e87992738f61db90601
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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