[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]=1A 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.
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