Pyridine → N-(2-benzyloxy-5-cyanomethoxy-phenyl)-methanesulfonamide

HRID 1106734Notes

Reaction equation

HRID 1106734 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[O:5][CH2:6][C:7]#[N:8].N1C=CC=CC=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>O>[CH2:13]([O:12][C:11]1[CH:10]=[CH:9][C:4]([O:5][CH2:6][C:7]#[N:8])=[CH:3][C:2]=1[NH:1][S:27]([CH3:26])(=[O:29])=[O:28])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 18789661(3-Amino-4-benzyloxy-phenoxy)-acetonitrile

Product 1

HCID 18789708N-(2-benzyloxy-5-cyanomethoxy-phenyl)-methanesulfonamideYield 46.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 5.9 g of (3-amino-4-benzyloxy-phenoxy)-acetonitrile and 24 ml of pyridine was cooled in an ice bath and treated at a dropwise rate with 3.46 g of methanesulfonyl chloride and stirred for 1 hour. The mixture was treated with 5 ml of water, removed the ice bath, and stirred at room temperature for 30 minutes. The mixture was poured into ethyl acetate, ice added, acidified with concentrated hydrochloric acid, washed with brine, dried (MgSO4), and evaporated. The residue was purified on silica gel eluting with ethyl acetate/hexane (2:5) and obtained 3.57 g of N-(2-benzyloxy-5-cyanomethoxy-phenyl)-methanesulfonamide as a cream solid.

Workup

  1. customremoved the ice bath
  2. stirringstirred at room temperature for 30 minutes
  3. additionThe mixture was poured into ethyl acetate, ice
  4. additionadded
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue was purified on silica gel eluting with ethyl acetate/hexane (2:5)

Sources & evidence

ORD record
ord-1a328153f73049618216d42a3f0b91f0
Source dataset
uspto-grants-2000_05
Patent number
US06057349

Reaction notes

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