Hydrochloric Acid → HCID 59347093, compound

HRID 19980Notes

Reaction equation

HRID 19980 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[N+:25]([O-])=O)[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[C:11]([O:20][CH3:21])[CH:10]=1)=[O:7].[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>CO.C(OCC)(=O)C.[Pd].N1C=CC=CC=1>[CH3:28][S:29]([NH:25][C:24]1[CH:23]=[CH:22][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[C:11]([O:20][CH3:21])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[O:2][CH3:1])(=[O:31])=[O:30]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 593470983-methoxy-4-nitro-N-(4-methanesulfonylamino-3-methoxyphenyl)benzamide

Product 1

HCID 59347093HCID 59347093, compoundYield 100%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-methoxy-4-nitro-N-(4-methanesulfonylamino-3-methoxyphenyl)benzamide (2.03 g) in methanol (50 ml) and ethyl acetate (50 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 (5 ml) and cooled to 0° C. when methanesulfonyl chloride (1 ml) was added, the mixture was kept at 0° C. for a further 2 hours then brought to R.T. for 1 h. The mixture was poured onto ice (50 g) and hydrochloric acid (3M, 50 g), the resultant brown solid filtered and washed with water to give 4-methanesulfonylamino-3-methoxy-N-(4-methanesulfonylamino-3-methoxyphenyl)benzamide (2.1 g, 100%) as a pale brown 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. filtrationthe resultant brown solid filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-064836f57209449392035c7f1e76111e
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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