Water → HCID 23511885, compound

HRID 350574Notes

Reaction equation

HRID 350574 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1)(=O)=O.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CC#N>[C:20]1([NH:19][CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 23512086HCID 23512086, compound

Product 1

HCID 23511885HCID 23511885, compoundYield 82.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 4-[2-(methanesulfonyloxy)ethoxy]benzoate (2.74 g, 10 mmol) in MeCN (50 ml), was added aniline (9.1 ml, 100 mmol) at rt. The reaction was stirred for 64 hours at reflux. The mixture was poured into H2O (200 mL), extracted with EtOAc (100 mL×2), dried over MgSO4. After removal of the solvent in vacuo, the unreacted aniline was removed in vacuo by co-evaporation with toluene (10 mL×3) at 80° C. The residue was chromatographed on silica gel (middle pressure chromatography system: YAMAZEN YFLC-5404-FC, f50 mm×150 mm, CHCl3) to give methyl 4-[2-(N-phenylamino)ethoxy]benzoate (2.23 g, 82%) as a colorless oil. 1H-NMR (CDCl3) δ 3.56 (t, J=5.1 Hz, 2 H), 3.90 (s, 3 H), 4.21 (t, J=5.1 Hz, 2), 6.68 (dd, J=1.0 Hz, 8.6 Hz, 2 H), 6.75 (t, J=7.3 Hz, 1 H), 7.20 (AB type d, J=7.3 Hz, 2 H), 8.00 (d, J=9.1 Hz, 2 H); MS (ESI) m/z 272 (M++1).

Workup

  1. temperatureat reflux
  2. extractionextracted with EtOAc (100 mL×2)
  3. dry with materialdried over MgSO4
  4. customAfter removal of the solvent in vacuo
  5. customthe unreacted aniline was removed in vacuo by co-evaporation with toluene (10 mL×3) at 80° C
  6. customThe residue was chromatographed on silica gel (middle pressure chromatography system: YAMAZEN YFLC-5404-FC, f50 mm×150 mm, CHCl3)

Sources & evidence

ORD record
ord-66a3e645b1aa4a9f9efc3615704260ca
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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