Ammonium Chloride → 3-(1,1-Dioxo-thiomorpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acid methyl ester

HRID 878352Notes

Reaction equation

HRID 878352 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][S:31](=[O:35])(=[O:34])[CH2:30][CH2:29]1.[NH4+].[Cl-]>C(Cl)Cl>[CH3:11][O:10][C:8](=[O:9])[C:7]1[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=[C:5]([S:2]([N:28]2[CH2:33][CH2:32][S:31](=[O:35])(=[O:34])[CH2:30][CH2:29]2)(=[O:4])=[O:3])[CH:6]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 6484228Thiomorpholine 1,1-dioxideHCID 62631505Methyl 3-(chlorosulfonyl)-5-(trifluoromethyl)benzoate

Product 1

HCID 706636143-(1,1-Dioxo-thiomorpholine-4-sulfonyl)-5-trifluoromethyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of methyl 3-(chlorosulfonyl)-5-(trifluoromethyl)benzoate (1 g, 3.3 mmol, Buttpark Ltd.) and DIPEA (641 mg, 866 μL, 4.96 mmol) in CH2Cl2 (4 mL) was added dropwise a solution of thiomorpholine 1,1-dioxide (447 mg, 3.3 mmol, CAS RN 39093-93-1) in CH2Cl2 (4.00 mL). After 90 minutes the suspension was poured on saturated aqueous NH4Cl solution and CH2Cl2 and the layers were separated. The aqueous layer was extracted twice with CH2Cl2. The organic layers were dried over MgSO4, filtered and evaporated. The compound was purified by silica gel chromatography on a 50 g column using an MPLC (Flasmaster) system eluting with a gradient of n-heptane:EtOAc (100:0 to 80:20). Light brown solid (0.99 g; 74%). MS (ESI): m/z=419.05 [M+NH4]+.

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. customevaporated
  6. customThe compound was purified by silica gel chromatography on a 50 g column
  7. washeluting with a gradient of n-heptane:EtOAc (100:0 to 80:20)

Sources & evidence

ORD record
ord-430e851556214ab2b119d87e01c64ce5
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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