Morpholine → Methyl 3-(morpholinosulfonyl)-5-(trifluoromethyl)benzoate

HRID 878293Notes

Reaction equation

HRID 878293 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3].CCN(C(C)C)C(C)C.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[NH4+].[Cl-]>C(Cl)Cl>[O:31]1[CH2:32][CH2:33][N:28]([S:2]([C:5]2[CH:6]=[C:7]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=2)[C:8]([O:10][CH3:11])=[O:9])(=[O:4])=[O:3])[CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 62631505Methyl 3-(chlorosulfonyl)-5-(trifluoromethyl)benzoate

Product 1

HCID 70663402Methyl 3-(morpholinosulfonyl)-5-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 3-(chlorosulfonyl)-5-(trifluoromethyl)benzoate (0.3 g, 991 μmol, Buttpark Ltd.) in CH2Cl2 (1.0 mL) were added DIPEA (192 mg, 260 μL, 1.49 mmol) and morpholine (86.4 mg, 86.4 μL, 991 μmol). The clear light yellow solution was stirred at room temperature for 1.3 hours and then poured on saturated aqueous NH4Cl solution and CH2Cl2. The layers were separated and the aqueous layer was extracted twice with CH2Cl2. The organic layers were dried over MgSO4, filtered, treated with silica gel and evaporated. Light brown solid (0.357 g; 91%). MS (EI): m/z=353 [M].

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted twice with CH2Cl2
  3. dry with materialThe organic layers were dried over MgSO4
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated

Sources & evidence

ORD record
ord-3fea0365e97a42d984a99a52fb7842c0
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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