Cesium carbonate → HCID 66666091, compound

HRID 474237Notes

Reaction equation

HRID 474237 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]>CN(C=O)C>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:2]=1[O:1][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])#[N:5]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2861482-Hydroxy-4-nitrobenzonitrileHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 66666091HCID 66666091, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 2-hydroxy-4-nitrobenzonitrile (4 g, 24.37 mmol) and cesium carbonate (11.91 g, 36.6 mmol) in DMF (40 mL) was added tert-butyl 3-bromopropylcarbamate (8.71 g, 36.6 mmol) at room temperature. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and the residue was taken in ethyl acetate (250 mL), washed with brine (2×100 mL). The organic layer was dried over anhydrous sodium sulphate and concentrated in vacuo to give tert-butyl 3-(2-cyano-5-nitrophenoxy)propylcarbamate (5 g, 63.8%) as a yellow solid. LC-MS (M+H)+=321.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.89-7.87 (1H, m), 7.81 (1H, s), 7.75 (1H, d, J=8.4 Hz), 4.76 (1H, br s), 4.27-4.24 (2H, t, J=6.4 Hz), 3.40-3.36 (2H, q, J=6.4, 12.8 Hz), 2.15-2.09 (2H, m), 1.43 (9H, s).

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with brine (2×100 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57dcae1c2dce4641bbc3c388fa94fe94
Source dataset
uspto-grants-2014_01
Patent number
US08637523B2

Reaction notes

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