Hydrochloric Acid → HCID 59347083, compound

HRID 19976Notes

Reaction equation

HRID 19976 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]([O:15][CH3:16])=[C:11]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:10]=1)=[O:7].[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>CO.[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]([O:15][CH3:16])=[C:11]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:10]=2)=[O:7])=[CH:4][C:3]=1[O:2][CH3:1])(=[O:31])=[O:30]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 59347113HCID 59347113, compound

Product 1

HCID 59347083HCID 59347083, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

A suspension of 3-methoxy-4-nitro-N-(3-methanesulfonylamino-4-methoxyphenyl)benzamide (1.4 g) 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 (5 ml) and cooled to 0° C. when methanesulfonyl chloride (0.5 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-(3-methanesulfonylamino-4-methoxyphenyl)benzamide (1.26 g, 86%) as a 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-b1db3f63309d44e8b3aafeecdda9f17f
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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