Methanesulfonyl chloride → 7-Methanesulphonamido-3-(5-methanesulphonamidobenzofur-2-yl-methyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

HRID 620728Notes

Reaction equation

HRID 620728 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[O:18][C:19]4[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][C:20]=4[CH:21]=3)[CH2:14][CH2:15][C:9]=2[CH:8]=1>N1C=CC=CC=1>[CH3:1][S:2]([NH:6][C:7]1[CH:28]=[CH:27][C:10]2[CH2:11][CH2:12][N:13]([CH2:16][C:17]3[O:18][C:19]4[CH:25]=[CH:24][C:23]([NH:26][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:22][C:20]=4[CH:21]=3)[CH2:14][CH2:15][C:9]=2[CH:8]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 212450567-Amino-3-(5-aminobenzofur-2-ylmethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

Product 1

HCID 212450587-Methanesulphonamido-3-(5-methanesulphonamidobenzofur-2-yl-methyl)-1,2,4,5-tetrahydro-3H-3-benzazepine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulphonyl cloride (0.28 ml) was added dropwise to a solution of 7-amino-3-(5-aminobenzofur-2-ylmethyl)-1,2,4,5-tetrahydro-3H-3-benzazepine (0.56 g) in pyridine (40 ml) cooled to 0° and the mixture was then stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue taken up in methylene chloride, washed three times with aqueous sodium bicarbonate and three times with brine. The organic layer was dried (Na2SO4), filtered and evaporated in vacuo to give an oil which was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 4%). The product-containing fractions were combined and evaporated to give the title compound as a foam, yield 0.56 g.

Workup

  1. temperaturecooled to 0°
  2. customThe solvent was evaporated in vacuo
  3. washwashed three times with aqueous sodium bicarbonate and three times with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give an oil which
  8. customwas purified by column chromatography on silica eluting with methylene chloride
  9. additioncontaining methanol (0% up to 4%)
  10. customevaporated

Sources & evidence

ORD record
ord-57bde151c9db4ab4881a84708e78ec4d
Source dataset
uspto-grants-1989_04
Patent number
US04822793

Reaction notes

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