N-(3-Benzyloxypropoxymethyl)-2,4,6-trichloro-N-methylbenzenesulfonamide → 2,4,6-trichloro-N-(3-hydroxypropoxymethyl)-N-methylbenzenesulfonamide

HRID 424625Notes

Reaction equation

HRID 424625 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][N:14]([CH3:27])[S:15]([C:18]1[C:23]([Cl:24])=[CH:22][C:21]([Cl:25])=[CH:20][C:19]=1[Cl:26])(=[O:17])=[O:16])C1C=CC=CC=1>[Pd].C1COCC1>[Cl:26][C:19]1[CH:20]=[C:21]([Cl:25])[CH:22]=[C:23]([Cl:24])[C:18]=1[S:15]([N:14]([CH2:13][O:12][CH2:11][CH2:10][CH2:9][OH:8])[CH3:27])(=[O:16])=[O:17]

Participants

4

Reactant 1

HCID 66703421N-(3-Benzyloxypropoxymethyl)-2,4,6-trichloro-N-methylbenzenesulfonamide

Product 1

HCID 667033602,4,6-trichloro-N-(3-hydroxypropoxymethyl)-N-methylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10% palladium on charcoal (350 mg) was added to a soln. of N-(3-benzyloxypropoxymethyl)-2,4,6-trichloro-N-methylbenzenesulfonamide (2.60 g, 5.7 mmol) in THF (100 ml) under argon and hydrogenation was carried out at RT under 3 bar. The reaction soln. was then filtered through Celite, the residue on the filter was washed with THF (50 ml) and the filtrate was concentrated i. vac. The crude product (1.63 g) was purified by means of flash chromatography with cyclohexane/EtOAc (1:1).

Workup

  1. customwas carried out at RT under 3 bar
  2. filtrationwas then filtered through Celite
  3. washthe residue on the filter was washed with THF (50 ml)
  4. concentrationthe filtrate was concentrated i
  5. customThe crude product (1.63 g) was purified by means of flash chromatography with cyclohexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-a1a1674fe6aa4c6090790ea7aaaf5afb
Source dataset
uspto-grants-2012_01
Patent number
US08106055B2

Reaction notes

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