Methanol → HCID 59347086, compound

HRID 19977Notes

Reaction equation

HRID 19977 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[C:15]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH:14]=2)=[O:11])=[CH:8][C:7]=1[O:28]C)(=[O:4])=[O:3].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:28][C:7]1[CH:8]=[C:9]([CH:26]=[CH:27][C:6]=1[NH:5][S:2]([CH3:1])(=[O:3])=[O:4])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([NH:21][S:22]([CH3:25])(=[O:23])=[O:24])[CH:14]=1)=[O:11]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 59347083HCID 59347083, compound

Product 1

HCID 59347086HCID 59347086, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 4-methanesulfonylamino-3-methoxy-N-(3-methanesulfonylamino-4-methoxyphenyl)benzamide (1.25 g) in dry CH2Cl2 (50 ml) under nitrogen, was added boron tribromide (1.5 ml) then stirring continued for a further 20 hours. Methanol (50 ml) was added carefully, then the solvent evaporated in vacuo to a volume of 1 ml, this was repeated 2 more times. Purification by column chromatography over silica gel eluting with chloroform containing methanol (10-20%) gave 3-hydroxy-4-methanesulfonylamino-N-(3-methanesulfonylamino-4-hydroxyphenyl)benzamide (143 mg, 15%) as an off-white solid.

Workup

  1. customthe solvent evaporated in vacuo to a volume of 1 ml
  2. customPurification by column chromatography over silica gel eluting with chloroform
  3. additioncontaining methanol (10-20%)

Sources & evidence

ORD record
ord-8e5b04f7125d40a39a2cc4d4836c7d8b
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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