반응 #48251

반응 방정식

methanesulfonyl chloride

4-methoxy-3-nitro-N-(4-methanesulfonylamino-3-methoxyphenyl)benzamide

hydrochloric acid

dichloromethane

→

product

4-Methoxy-3-methanesulfonylamino-N-(3-methoxy-4-methanesulfonylaminophenyl)-benzamide

용매

pyridine

methanol

반응 조건

후처리

1. 1
   기타The solvents were removed in vacuo
2. 2
   기타to give a brown gum
3. 3
   workup.ADDITIONwas added
4. 4
   workup.WAITthen brought to R.T. for 1 h
5. 5
   기타the organic layer separated
6. 6
   기타dried
7. 7
   기타evaporated in vacuo

실험 절차

A suspension of 4-methoxy-3-nitro-N-(4-methanesulfonylamino-3-methoxyphenyl)benzamide (100 mg) in methanol (20 ml) was stirred under hydrogen with palladium on carbon (10%, 50 mg) for 18 hours. The solvents were removed in vacuo to give a brown gum. The residue was dissolved in pyridine (0.5 ml) and cooled to 0° C. when methanesulfonyl chloride (0.1 ml) was added, the mixture was kept at 0° C. for a further 30 minutes then brought to R.T. for 1 h. Dilute hydrochloric acid (10 ml, 1M) and dichloromethane were added, the organic layer separated, dried and evaporated in vacuo to give the product as a brown gum. Purification by column chromatography over silica gel eluting with dichloromethane containing ethyl acetate (0-100%) gave 3-methanesulfonylamino-4-methoxy-N-(3-methanesulfonylamino-4-methoxyphenyl)benzamide (65 mg, 56%) as a white solid.

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