Methylamine → 4-(4-hydroxy-phenoxy)-N-methyl-benzamide

HRID 49154Notes

Reaction equation

HRID 49154 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[CH2:18]([N:20](CC)CC)C.COC(Cl)=O.CN>O.O1CCCC1>[OH:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([NH:20][CH3:18])=[O:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 6155424-(4-Hydroxy-phenoxy)-benzoic acid

Product 1

HCID 181840264-(4-hydroxy-phenoxy)-N-methyl-benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(4-Hydroxy-phenoxy)-benzoic acid (0.25 g, 1.09 mmol), triethylamine (0.15 mL, 1.07 mmol) and tetrahydrofuran (THF) (5.0 mL) at 0° C. was added methylchloroformate (0.084 mL, 0.10 g, 1.1 mmol). After stirring for 15 minutes, excess methylamine was added via a sparge tube, and stirring was continued for 10 minutes. The mixture was diluted with water, extracted three times with ethyl acetate, and the combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo, affording 1 4-(4-Hydroxy-phenoxy)-N-methyl-benzamide as a colorless syrup.

Workup

  1. stirringstirring
  2. waitwas continued for 10 minutes
  3. extractionextracted three times with ethyl acetate
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6ab78729e17448358004cb22c51c592f
Source dataset
uspto-grants-2004_03
Patent number
US06706723B2

Reaction notes

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