Benzylamine → HCID 67263836, compound

HRID 1041130Notes

Reaction equation

HRID 1041130 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-0efbc2918d7d4824b006f73bb876431e
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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