Hydrochloric Acid → 5-Chloro-2-hydroxy-N-[(4-phenoxyphenyl)methyl]benzamide

HRID 1986155Notes

Reaction equation

C1N=CN([C:6]([N:8]2C=N[CH:10]=[CH:9]2)=[O:7])C=1.[O:13]([C:20]1[CH:27]=[CH:26]C(CN)=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[ClH:28]>CN(C=O)C>[Cl:28][C:17]1[CH:16]=[CH:15][C:14]([OH:13])=[C:19]([CH:18]=1)[C:6]([NH:8][CH2:9][C:10]1[CH:22]=[CH:21][C:20]([O:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:27][CH:26]=1)=[O:7]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-chlorocsalicyclic acid in anhydrous DMF (5 mL) was added CDI (0.167 g, 1.043 mmol), at 25° C. under nitrogen atmosphere. The reaction mixture was stirred for another 2 h at 25° C. To the above reaction mixture 4-phenoxy benzylamine was added and stirring continued overnight. At the end of this period 2N HCl (20 mL) was added and extracted with ethyl acetate (2×20 mL). The combined ethyl acetate layer was washed with water (2×30 mL), dried (Na2SO4), filtered and solvent was evaporated. The resulting crude material was chromatographed over silica gel using mixture of ethyl acetate and hexanes (3:7) to give title product (0.121 g, 27%). 1H NMR (CDCl3) δ 4.60 (d, 2H), 6.44 (bs, 1H), 6.90-7.37 (m, 12H), 12.21 (s, 1H),

Workup

customat 25° C.
stirringstirring continued overnight
extractionextracted with ethyl acetate (2×20 mL)
washThe combined ethyl acetate layer was washed with water (2×30 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
customsolvent was evaporated
customThe resulting crude material was chromatographed over silica gel using mixture of ethyl acetate and hexanes (3:7)

Sources & evidence

ORD record: ord-43ebe7c4e1754bb999c6c181a862dac7
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547804B2

Reaction notes

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