Methanol → 3-Hydroxy-4-methanesulfonylamino-N-(3,4-dihydroxyphenyl)benzamide

HRID 19968Notes

Reaction equation

HRID 19968 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15]C[O:17][C:11]=2[CH:10]=1)=[O:7].B(Br)(Br)Br.CO>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:17])[CH:10]=1)=[O:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 587033643-Methoxy-4-methanesulfonylamino-N-(3,4-methylenedioxyphenyl)benzamide

Product 1

HCID 116744773-Hydroxy-4-methanesulfonylamino-N-(3,4-dihydroxyphenyl)benzamideYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of 3-Methoxy-4-methanesulfonylamino-N-(3,4-methylenedioxyphenyl)benzamide (200 mg) in dry CH2Cl2 (20 ml) under nitrogen, was added boron tribromide (0.3 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-(3,4-dihydroxyphenyl)benzamide (DC51-DB) (65 mg, 34%) as pale brown crystals.

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-1686814b05de4bdab2ffcff5ed7dbd2a
Source dataset
uspto-grants-2010_06
Patent number
US07745490B2

Reaction notes

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