Cesium carbonate → HCID 22619992, compound

HRID 840651Notes

Reaction equation

HRID 840651 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[NH2:5].[CH3:10][O:11][CH2:12][CH2:13]Br.C([O-])([O-])=O.[Cs+].[Cs+].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH3:9][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[CH:3][C:2]=1[O:1][CH2:13][CH2:12][O:11][CH3:10]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 178185-Amino-2-methylphenolHCID 809722-Bromoethyl methyl etherHCID 516892Sodium Bicarbonate

Product 1

HCID 22619992HCID 22619992, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

22.0 g of 3-hydroxy-4-methylaniline, 24.9 g of 2-bromoethyl methyl ether and 233 g of Cs2CO3 are dissolved in 570 ml of DMF and stirred at 40° C. for 8 h. 3 l of a 10% aqueous sodium hydrogencarbonate solution are added, and the mixture is extracted 6 times with 750 ml of EA each time and washed twice with 1 l of a 10% aqueous sodium hydrogencarbonate solution each time. It is dried over sodium sulfate and the solvent is removed in vacuo. 32.9 g of a yellow oil are obtained, which is employed further as such.

Workup

  1. extractionthe mixture is extracted 6 times with 750 ml of EA each time
  2. washwashed twice with 1 l of a 10% aqueous sodium hydrogencarbonate solution each time
  3. dry with materialIt is dried over sodium sulfate
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-62c645f3d6fb4a6b91371e91ad9da207
Source dataset
uspto-grants-2002_04
Patent number
US06369069B1

Reaction notes

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