Water → HCID 54279435, compound

HRID 399854Notes

Reaction equation

HRID 399854 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])=[O:4].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(OCC)(=O)C.O>ClCCl.O1CCCC1>[O:24]1[CH2:25][CH2:26][N:21]([CH2:2][C:3]([NH:5][C:6]2[CH:7]=[C:8]([CH:13]=[C:14]([N:16]3[CH:20]=[CH:19][CH:18]=[CH:17]3)[CH:15]=2)[C:9]([O:11][CH3:12])=[O:10])=[O:4])[CH2:22][CH2:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 8857Ethyl AcetateHCID 18945265HCID 18945265, compound

Product 1

HCID 54279435HCID 54279435, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 3-bromoacetylamino-5-(pyrrol-1-yl)benzoate (0.5 g) and morpholine (0.28 ml) in dichloromethane (5 ml) and tetrahydrofuran (7 ml) was stirred for 17 hours at room temperature. The reaction mixture was poured into the mixture of ethyl acetate and water. The organic layer was successively washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with chloroform. The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-morpholinoacetylamino-5-(pyrrol-1-yl)benzoate (0.48 g).

Workup

  1. washThe organic layer was successively washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography on silica gel eluting with chloroform
  5. additionThe eluted fractions containing the desired product
  6. customwere collected
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-d9a0503fcaf74866a14ce0c58c821893
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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