Benzylamine → HCID 67263836, compound

HRID 1687435Notes

Reaction equation

HRID 1687435 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13].[CH2:18]([NH2:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:25][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[S:12]([N:15]([CH3:17])[CH3:16])(=[O:14])=[O:13])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 60639860HCID 60639860, compound

Product 1

HCID 67263836HCID 67263836, compound

Procedure

A solution of 2-Chloro-N,N-dimethyl-5-trifluoromethyl-benzenesulfonamide (2.10 g, 0.00730 mol) in Benzylamine (5 mL, 0.04 mol) was heated at 100° C. for 5 hours. The benzylamine was evaporated under reduced pressure. The residue was partitioned between water (50 mL) and ethyl acetate (50 mL). The organic layer was washed with water (3×50 mL), dried over magnesium sulfate, filtered and evaporated. The material was purified via silica gel chromatography using 0% 25% Ethyl Acetate:Hexane solvent gradient. 2-Benzylamino-N,N-dimethyl-5-trifluoromethyl-benzenesulfonamide isolated as a pale yellow solid (1.84 g, 70%).

Workup

  1. customThe benzylamine was evaporated under reduced pressure
  2. customThe residue was partitioned between water (50 mL) and ethyl acetate (50 mL)
  3. washThe organic layer was washed with water (3×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe material was purified via silica gel chromatography

Sources & evidence

ORD record
ord-187a01473b9c4985909bed7d9f8d566a
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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