Hydrochloric Acid → HCID 59347114, compound

HRID 19973Notes

Reaction equation

HRID 19973 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:12]([O:21][CH3:22])[CH:11]=2)=[O:8])=[CH:5][C:4]=1[N+:25]([O-])=O.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl.ClCCl>CO.[Pd].N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[C:12]([O:21][CH3:22])[CH:11]=2)=[O:8])=[CH:5][C:4]=1[NH:25][S:29]([CH3:28])(=[O:31])=[O:30]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 40262664HCID 40262664, compound

Product 1

HCID 59347114HCID 59347114, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

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.

Workup

  1. customThe solvents were removed in vacuo
  2. customto give a brown gum
  3. additionwas added
  4. waitthen brought to R.T. for 1 h
  5. customthe organic layer separated
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-67032c0a6a6f4b9d8cd4ada6f38df143
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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