4-Methylmorpholine → HCID 54501570, compound

HRID 442904Notes

Reaction equation

HRID 442904 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9](Cl)(=[O:11])=[O:10].[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([CH:27]=[C:28]([CH3:30])[CH:29]=1)[NH2:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CN1CCOCC1>ClCCl>[CH2:15]([O:22][C:23]1[CH:24]=[C:25]([NH:26][S:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:2]([F:14])([F:13])[F:1])(=[O:11])=[O:10])[CH:27]=[C:28]([CH3:30])[CH:29]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 1366162-Trifluoromethylbenzenesulphonyl chlorideHCID 22722681HCID 22722681, compound

Product 1

HCID 54501570HCID 54501570, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-Trifluoromethylbenzenesulfonyl chloride (490 mg, 2.0 mmol) was added to a solution of 3-benzyloxy-5-methylaniline (426 mg, 2.0 mmol), as prepared in the preceding step, and N-methylmorpholine (0.5 mL) in dichloromethane (10 mL). The mixture was stirred at ambient temperature overnight. After adding additional dichloromethane (100 mL), the dichloromethane solution was washed with saturated aqueous NaHCO3 (2×50 mL), 10% HCl (2×50 mL), and brine (2×50 mL), and dried over Na2SO4. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography (4:1 dichloromethane/hexane) to give the title compound as white solid (700 mg, 83%). 1H-NMR (300 MHz, CDCl3) δ 7.93 (d, J=7.8 Hz, 1 H), 7.85 (d, J=7.3 Hz, 1 H), 7.63 (t, J=7.7 Hz, 1 H), 7.53 (t,J=7.7 Hz, 1 H), 7.38 (m, 5 H), 6.60 (s, 1 H), 6.55 (s, 2 H), 6.40 (s, 1 H), 4.98 (s, 2 H), 2.20 (s, 3 H).

Workup

  1. washthe dichloromethane solution was washed with saturated aqueous NaHCO3 (2×50 mL), 10% HCl (2×50 mL), and brine (2×50 mL)
  2. dry with materialdried over Na2SO4
  3. customAfter evaporating the solvent in vacuo
  4. customthe residue was purified by flash column chromatography (4:1 dichloromethane/hexane)

Sources & evidence

ORD record
ord-cbcaba72652a4d53be7ceaf65be94ae7
Source dataset
uspto-grants-1999_04
Patent number
US05891909

Reaction notes

Loading…