Sodium hydride → HCID 68828889, compound

HRID 2100378Notes

Reaction equation

HRID 2100378 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].I[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[H-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6425184Methyl 4-Bromo-3-hydroxybenzoateHCID 111491684-(2-iodoethyl)morpholine

Product 1

HCID 68828889HCID 68828889, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 4-bromo-3-hydroxybenzoate (143 mg) and 4-(2-iodoethyl)morpholine.HCI (189 mg) were combined in DMF (10 ml). Sodium hydride (55 mg, 60% dispersion in mineral oil) was added and the reaction heated at 80° C. under nitrogen for 5 hours. The reaction was quenched with water (10 ml) and the solvent evaporated under vacuum. Ethyl acetate/chloroform (1:1, 30 ml) and water (30 ml) were added to the residue resulting in precipitation of a solid, which was filtered off and washed with ether. The solid was partitioned between ethyl acetate/chloroform (1:1, 2×50 ml) and aqueous sodium hydrogen carbonate solution (1 M, 50 ml). The organic layers were combined, dried over a hydrophobic filter and evaporated to give methyl 4-bromo-3-{[2-(4-morpholinyl)ethyl]oxy}benzoate as a yellow gel (103 mg).

Workup

  1. customThe reaction was quenched with water (10 ml)
  2. customthe solvent evaporated under vacuum
  3. additionEthyl acetate/chloroform (1:1, 30 ml) and water (30 ml) were added to the residue
  4. customresulting in precipitation of a solid, which
  5. filtrationwas filtered off
  6. washwashed with ether
  7. customThe solid was partitioned between ethyl acetate/chloroform (1:1, 2×50 ml) and aqueous sodium hydrogen carbonate solution (1 M, 50 ml)
  8. customdried over
  9. filtrationa hydrophobic filter
  10. customevaporated

Sources & evidence

ORD record
ord-1b70555b08544b1fbccaf5c9aad240cf
Source dataset
uspto-grants-2009_08
Patent number
US07572790B2

Reaction notes

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