Methanesulfonyl chloride → HCID 68866370, compound

HRID 332577Notes

Reaction equation

HRID 332577 reaction equation
Cl.[Cl:2]C1C=C(C=CC=1)OC1C=C(C=CC=1OC)CC1C=CC(NS(C)(=O)=O)=NC=1.[Cl:30][C:31]1[CH:32]=[C:33]([CH:51]=[CH:52][CH:53]=1)[O:34][C:35]1[CH:36]=[C:37]([CH:46]=[CH:47][C:48]=1[O:49][CH3:50])[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([NH2:45])=[N:43][CH:44]=1.CS(Cl)(=O)=O>N1C=CC=CC=1>[ClH:2].[Cl:30][C:31]1[CH:32]=[C:33]([CH:51]=[CH:52][CH:53]=1)[O:34][C:35]1[CH:36]=[C:37]([CH:46]=[CH:47][C:48]=1[O:49][CH3:50])[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([NH2:45])=[N:43][CH:44]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 57701104HCID 57701104, compoundHCID 68865856HCID 68865856, compound

Product 1

HCID 68866370HCID 68866370, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

N-{5-[3-(3-Chloro-phenoxy)-4-methoxy-benzyl]-pyridin-2-yl}-methanesulfonamide HCl salt, P-09. To a 25 mL vial which contained 5-[3-(3-chloro-phenoxy)-4-methoxy-benzyl]-pyridin-2-ylamine P-05 (170 mg, 0.5 mmol) in pyridine (8 mL) was added methanesulfonyl chloride (144 mg, 1.3 mmol) at rt. The mixture was stirred at rt for 24 h. The mixture was poured into 50 mL ice-water and extracted with ethyl acetate, washed with water 1 N HCl, brine, and dried over Na2SO4. After it was concentrated in vacuo, the residue was purified by chromatography on silica gel with ethyl acetate/hexane as eluent to yield 80 mg (38% yield) of the desired product, P-09, using 2N HCl in ether was to convert into its HCl salt 50 mg (60% yield).

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water 1 N HCl, brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter it was concentrated in vacuo
  5. customthe residue was purified by chromatography on silica gel with ethyl acetate/hexane as eluent

Sources & evidence

ORD record
ord-8ade492876ec449b9145d1856c9a36d9
Source dataset
uspto-grants-2014_11
Patent number
US08877816B2

Reaction notes

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